dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-88be1d9b0db14939840bd365ed48fe65 | CN(C)C=O.Clc1ccc2ccccc2n1>>O=Cc1cc2ccccc2nc1Cl | ClC1=NC2=CC=CC=C2C=C1.C(C)(C)NC(C)C.[Li]CCCC.CN(C=O)C>>ClC1=NC2=CC=CC=C2C=C1C=O | CN(C)[CH:2]=[O:1].[cH:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[Cl:13]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[Cl:13] | CN(C)C=O.Clc1ccc2ccccc2n1 | O=Cc1cc2ccccc2nc1Cl | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 2fb6a63f37a90389382989ea42f8436574f9d339310d3a9ddc749d75d88d7d6b | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccc2ncccc2c1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[cH;D2;+0:9]:1>>[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:1-[CH;D2;+0:1]=[O;D1;H0:2] | 92.2 | [{"value": 92.0, "product": "ClC1=NC2=CC=CC=C2C=C1C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "ClC1=NC2=CC=CC=C2C=C1C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a solution of 0.46 mL (3.30 mmol) of diisopropylamine in 8 mL of THF at 0.C was added 1.53 mL (3.30 mmol) of n-BuLi dropwise. After 20 min the solution was cooled to -78° C. and 2-chloroquinoline (491 mg, 3.0 mmol) was added neat. The mixture was stirred at -78° C. for 30 min, then dimethylformamide (0.39 mL, 5.04 m... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | C1CCOC1 | -78 | 0.5 | CN(C)C=O.Clc1ccc2ccccc2n1>C1CCOC1>O=Cc1cc2ccccc2nc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c63ace3342d84bbd8c5c2007a1065d40 | O=Cc1cc2ccccc2nc1I>>OCc1cc2ccccc2nc1I | IC1=NC2=CC=CC=C2C=C1C=O>>OCC=1C(=NC2=CC=CC=C2C1)I | [O:1]=[CH:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13]>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13] | O=Cc1cc2ccccc2nc1I | OCc1cc2ccccc2nc1I | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc2ncccc2c1 | [I;D1;H0:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]>>[I;D1;H0:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8] | 84 | [{"value": 84.0, "product": "OCC=1C(=NC2=CC=CC=C2C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.7, "product": "OCC=1C(=NC2=CC=CC=C2C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 2-iodo-3-quinolinecarboxaldehyde (595 mg, 2 10 mmol) in 40 mL of CH3OH at 0° C. was added NaBH (86 mg, 2.31 mmol), and the mixture was stirred at 0° C. for 30 min. After concentrating the mixture to approximately one-half of its original volume, water (30 mL) was added and the mixture was allow... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccc2ncccc2c1 | null | CO | 0 | 0.5 | O=Cc1cc2ccccc2nc1I>CO>OCc1cc2ccccc2nc1I |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-edd23c2804654fc28bceec3530087a78 | O=C1CCC(=O)N1Cl.OCc1cc2ccccc2nc1I>>ClCc1cc2ccccc2nc1I | C(=O)(O)[O-].[Na+].OCC=1C(=NC2=CC=CC=C2C1)I.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ClN1C(CCC1=O)=O>>ClCC=1C(=NC2=CC=CC=C2C1)I | O=C1CCC(=O)N1[Cl:1].O[CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13]>>[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11][c:12]1[I:13] | O=C1CCC(=O)N1Cl.OCc1cc2ccccc2nc1I | ClCc1cc2ccccc2nc1I | null | null | CN(C)C=O | Functional Group Interconversion | Alcohol to chloride_Other | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccc2ncccc2c1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[I;D1;H0:5]):[#7;a:6]:[c:7].O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:8]>>[Cl;H0;D1;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[I;D1;H0:5]):[#7;a:6]:[c:7] | 84 | [{"value": 84.0, "product": "ClCC=1C(=NC2=CC=CC=C2C1)I", "details": "PERCENTYIELD", "is_desired": false}] | -23 | CELSIUS | 1 | HOUR | To a stirred mixture of 3-hydroxymethyl-2-iodoquinoline prepared in accordance with Example 10 above (350 mg, 1.23 mmol) and triphenylphosphine (483 mg, 1.84 mmol) in 10 mL of dry DMF at -23° C. was added N-chlorosuccinimide (246 mg, 1.84 mmol), and the mixture was stirred for 1 h at -23° C. After the addition of 40 mL... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccc2ncccc2c1 | HO- | CN(C)C=O | -23 | 1 | O=C1CCC(=O)N1Cl.OCc1cc2ccccc2nc1I>CN(C)C=O>ClCc1cc2ccccc2nc1I |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aed351363b3f4779b0e84261ee5bce75 | CCOC(=O)c1cc2ccccc2[nH]1>>COC(=O)C1Cc2ccccc2N1 | [Mg].N1C(=CC2=CC=CC=C12)C(=O)OCC.[OH-].[NH4+].[Mg]>>N1C(CC2=CC=CC=C12)C(=O)OC | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[nH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13]1 | CCOC(=O)c1cc2ccccc2[nH]1 | COC(=O)C1Cc2ccccc2N1 | null | null | CO | Miscellaneous | OtherReaction | d9ce7bddaf4a65dd9ffd6a84fd8ad2b32692d0f88bb31fffb1f1fad429fdb653 | 4cbcbcdde488f736a7c82e30d7aeccb07f6bf0f595a2869ce6c1254ae9c262b5 | c1ccc2c(c1)CCN2 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:10]):[nH;D2;+0:11]:1>>[CH3;D1;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9](:[c:10])-[NH;D2;+0:11]-1 | null | [] | null | null | null | null | Magnesium turnings (3.60 g) are added to a mixture of ethyl indole-2-carboxylate (I, Aldrich Chemical, 13.963 g) in methanol (200 ml). After evolution of gas has started, the mixture is placed in an ice bath and the temperature kept below 45°. After 4.5 hours all of the magnesium is used up and the temperature is 7°. A... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester.Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | CO | null | null | CCOC(=O)c1cc2ccccc2[nH]1>CO>COC(=O)C1Cc2ccccc2N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-671179d93c62438b8725da5483797094 | CCOC(=O)c1cc2ccccc2[nH]1>>COC(=O)C1Cc2ccccc2N1 | [OH-].[NH4+].[Mg].N1C(=CC2=CC=CC=C12)C(=O)OCC.Cl.S([O-])(O)(=O)=O.[Na+].[OH-].[NH4+]>>N1C(CC2=CC=CC=C12)C(=O)OC | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[nH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[NH:13]1 | CCOC(=O)c1cc2ccccc2[nH]1 | COC(=O)C1Cc2ccccc2N1 | null | null | CO.C(Cl)Cl | Miscellaneous | OtherReaction | d9ce7bddaf4a65dd9ffd6a84fd8ad2b32692d0f88bb31fffb1f1fad429fdb653 | 4cbcbcdde488f736a7c82e30d7aeccb07f6bf0f595a2869ce6c1254ae9c262b5 | c1ccc2c(c1)CCN2 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7](:[c:8]):[c:9](:[c:10]):[nH;D2;+0:11]:1>>[CH3;D1;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9](:[c:10])-[NH;D2;+0:11]-1 | null | [] | null | null | 10 | MINUTE | Magnesium turnings (6.449 g) are added to a suspension of ethyl indole-2-carboxylate (I, Aldrich, 25.083 g) in methanol (freshly opened, HPLC grade, 350 ml). The mixture is stirred at 24° for 10 minutes, then placed in an ice bath. After stirring for 15 minutes in the ice bath, there is much gas evolution and the tempe... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester.Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | Other | CO.C(Cl)Cl | null | 0.166667 | CCOC(=O)c1cc2ccccc2[nH]1>CO.C(Cl)Cl>COC(=O)C1Cc2ccccc2N1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-31cb662b70f24c10af54b3ec7813782c | O=C(OCc1ccccc1)N1c2ccccc2CC1CO>>O=CC1Cc2ccccc2N1C(=O)OCc1ccccc1 | C(C)N(CC)CC.CS(=O)C.C(C(=O)Cl)(=O)Cl.C(C1=CC=CC=C1)OC(=O)N1C(CC2=CC=CC=C12)CO>>C(C1=CC=CC=C1)OC(=O)N1C(CC2=CC=CC=C12)C=O | [OH:1][CH2:2][CH:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[N:11]1[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[O:1]=[CH:2][CH:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[N:11]1[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | O=C(OCc1ccccc1)N1c2ccccc2CC1CO | O=CC1Cc2ccccc2N1C(=O)OCc1ccccc1 | null | null | C(Cl)Cl.O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C(OCc1ccccc1)N1CCc2ccccc21 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[C:6](-[CH2;D2;+0:7]-[OH;D1;+0:8])-[C:9]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[c:5])-[C:6](-[CH;D2;+0:7]=[O;H0;D1;+0:8])-[C:9] | null | [] | null | null | 20 | MINUTE | Dimethyl sulfoxide (2.75 ml) is added to a solution of oxalyl chloride (1.7 ml) in methylene chloride (45 ml) at -78° under nitrogen via cannula over six minutes. After 20 minutes, (±) 1-benzyloxycarbonyl-2-hydroxymethylindoline (IV, EXAMPLE 4, 5.003 g) in methylene chloride (20 ml) is added via cannula over 12 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2c(c1)CC[NH]2.c1ccccc1 | null | C(Cl)Cl.O | null | 0.333333 | O=C(OCc1ccccc1)N1c2ccccc2CC1CO>C(Cl)Cl.O>O=CC1Cc2ccccc2N1C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-85b07e5110d544a984eac5be63d4a683 | N#CC(O)C1Cc2ccccc2N1C(=O)OCc1ccccc1>>NCC(O)C1Cc2ccccc2N1C(=O)OCc1ccccc1 | Cl.[OH-].[Na+].B.CSC.C(C1=CC=CC=C1)OC(=O)N1C(CC2=CC=CC=C12)C(O)C#N.CSC.B>>C(C1=CC=CC=C1)OC(=O)N1C(CC2=CC=CC=C12)C(CN)O | [N:1]#[C:2][CH:3]([OH:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[N:13]1[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[NH2:1][CH2:2][CH:3]([OH:4])[CH:5]1[CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[N:13]1[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1 | N#CC(O)C1Cc2ccccc2N1C(=O)OCc1ccccc1 | NCC(O)C1Cc2ccccc2N1C(=O)OCc1ccccc1 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(OCc1ccccc1)N1CCc2ccccc21 | [#7:1]-[C:2]-[C:3](-[O;D1;H1:4])-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]>>[#7:1]-[C:2]-[C:3](-[O;D1;H1:4])-[CH2;D2;+0:5]-[NH2;D1;+0:6] | null | [] | null | null | null | null | Borane-dimethylsulfide (2M, 0.85 ml) is added to a mixture of (±) 1-benzyloxycarbonyl-2-(1-cyano-1-hydroxymethyl)indoline [VI diastereomer B, EXAMPLE 6, 0.431 g] in refluxing tetrahydrofuran (5 ml) slowly over 6 minutes. After one hour additional borane-dimethyl sulfide (2M, 0.5 ml) is added over 2 minutes. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2c(c1)CC[NH]2.c1ccccc1 | null | O1CCCC1 | null | null | N#CC(O)C1Cc2ccccc2N1C(=O)OCc1ccccc1>O1CCCC1>NCC(O)C1Cc2ccccc2N1C(=O)OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dbc1ae6b977c4446b64e652ac5a7f2cb | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O>>CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 | C(C)(=O)OC(C)=O.O=C1OC(C2N1C=1C=CC=CC1C2)CNC(C)=O.CS(=O)(=O)O.C(C)(=O)OC(C)=O.C([O-])(O)=O.[Na+].C([O-])(O)=O.[Na+]>>C(C)(=O)C1=CC=2CC3N(C2C=C1)C(OC3CNC(C)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:18][c:19]3[CH2:20][CH:21]12.CC(=O)O[C:15]([CH3:16])=[O:17]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c:14]([C:15]([CH3:16])=[O:17])[cH:18][c:19]3[CH2:20][CH:21]12 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O | CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 5f1653ab03bb4e49d2f440d8f3dfb59b2c775fce7479c2389a33196f7750a248 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | O=C1OCC2Cc3ccccc3N12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 1 | HOUR | A mixture of (±) (1S,9aS/1R,9aR) N-[(9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (X diastereomer B, EXAMPLE 11, 8 mg), methane sulfonic acid (0.5 ml), and acetic anhydride (10 μl) is stirred in methylene chloride (0.2 ml) from 0° to 20° for 19.5 hours. After this time the mixture is cooled in an ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | HO- | C(Cl)Cl | null | 1 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O>C(Cl)Cl>CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-7b19ffcc5e3d49d7a3afa6d58e690d43 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O>>CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 | C(C)(=O)OC(C)=O.O=C1OC(C2N1C=1C=CC=CC1C2)CNC(C)=O.C([O-])(O)=O.[Na+]>>C(C)(=O)C1=CC=2CC3N(C2C=C1)C(OC3CNC(C)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:18][c:19]3[CH2:20][CH:21]12.CC(=O)O[C:15]([CH3:16])=[O:17]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c:14]([C:15]([CH3:16])=[O:17])[cH:18][c:19]3[CH2:20][CH:21]12 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O | CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 | null | null | C(Cl)Cl.CS(=O)(=O)O | C-C Coupling | Friedel-Crafts acylation | 5f1653ab03bb4e49d2f440d8f3dfb59b2c775fce7479c2389a33196f7750a248 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | O=C1OCC2Cc3ccccc3N12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 20.5 | HOUR | Acetic anhydride (91 μl) is added to a mixture of (±) (1S,9aS/1R,9aR) N-[(9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (X diastereomer B, EXAMPLE 11, 74 mg) in methane sulfonic acid (1 ml) at 0° over 1 minute. The mixture is stirred for 20.5 hours and allowed to warm to 20°-25° during this time. A... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | HO- | C(Cl)Cl.CS(=O)(=O)O | null | 20.5 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O>C(Cl)Cl.CS(=O)(=O)O>CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1b744634cec94374ac2598be1eb4e1c6 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O>>CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 | C(C)(=O)OC(C)=O.O=C1OC(C2N1C=1C=CC=CC1C2)CNC(C)=O.CS(=O)(=O)OS(=O)(=O)C>>C(C)(=O)C1=CC=2CC3N(C2C=C1)C(OC3CNC(C)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:18][c:19]3[CH2:20][CH:21]12.CC(=O)O[C:15]([CH3:16])=[O:17]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c:14]([C:15]([CH3:16])=[O:17])[cH:18][c:19]3[CH2:20][CH:21]12 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O | CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 | null | null | C(Cl)Cl.CS(=O)(=O)O | C-C Coupling | Friedel-Crafts acylation | 5f1653ab03bb4e49d2f440d8f3dfb59b2c775fce7479c2389a33196f7750a248 | e8c3519869b9d5fd7c4ab2911407db4a86c645fb02749ed598ab3b129e3927f8 | O=C1OCC2Cc3ccccc3N12 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | null | [] | null | null | 3 | HOUR | Acetic anhydride (53 μl) is slowly added to a mixture of (±) N-[(9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (X diastereomer A, EXAMPLE 18, 21 mg), methanesulfonic anhydride (33 mg) in methylene chloride (0.1 ml) and methane sulfonic acid (0.50 ml) at 0°. The temperature is kept below 15° for 3 h... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ketone | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | HO- | C(Cl)Cl.CS(=O)(=O)O | null | 3 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.CC(=O)OC(C)=O>C(Cl)Cl.CS(=O)(=O)O>CC(=O)NCC1OC(=O)N2c3ccc(C(C)=O)cc3CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1f6e982b827e468188c3fc64dfc63777 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.O=C1CCC(=O)N1Br>>CC(=O)NCC1OC(=O)N2c3ccc(Br)cc3CC12 | O=C1OC(C2N1C=1C=CC=CC1C2)CNC(C)=O.BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>BrC1=CC=2CC3N(C2C=C1)C(OC3CNC(C)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:16][c:17]3[CH2:18][CH:19]12.O=C1CCC(=O)N1[Br:15]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]3[CH2:18][CH:19]12 | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.O=C1CCC(=O)N1Br | CC(=O)NCC1OC(=O)N2c3ccc(Br)cc3CC12 | null | null | C(C)#N | Functional Group Interconversion | Bromination | 69419bfecab157d58793faefaa082ae9172668ac88422babe0c9994bfbcc21c8 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C1OCC2Cc3ccccc3N12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | null | null | null | null | (±) (1S,9aS/1R,9aR) N-[(9,9a-Dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (X, diastereomer B, [SS,RR-trans], EXAMPLE 11, 299 mg) is dissolved in acetonitrile (10 ml). To this mixture N-bromosuccinimide (235 mg) and a catalytic amount of benzoylperoxide are added as solids to the mixture at 20°-25°. The... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)CC1COCN21.C1CCNC1 | c1ccc2c(c1)CC1COCN21 | c1ccc2c(c1)CC1COCN21 | HO- | C(C)#N | null | null | CC(=O)NCC1OC(=O)N2c3ccccc3CC12.O=C1CCC(=O)N1Br>C(C)#N>CC(=O)NCC1OC(=O)N2c3ccc(Br)cc3CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0b84c5d8a820414a8eea57ac247ba120 | CC(=O)NCC1OC(=O)N2c3ccc(Br)cc3CC12.OB(O)c1ccccc1>>CC(=O)NCC1OC(=O)N2c3ccc(-c4ccccc4)cc3CC12 | BrC1=CC=2CC3N(C2C=C1)C(OC3CNC(C)=O)=O.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>C1(=CC=CC=C1)C1=CC=2CC3N(C2C=C1)C(OC3CNC(C)=O)=O | Br[c:14]1[cH:13][cH:12][c:11]2[c:22]([cH:21]1)[CH2:23][CH:24]1[CH:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:7][C:8](=[O:9])[N:10]21.OB(O)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][CH:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[c... | CC(=O)NCC1OC(=O)N2c3ccc(Br)cc3CC12.OB(O)c1ccccc1 | CC(=O)NCC1OC(=O)N2c3ccc(-c4ccccc4)cc3CC12 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd] | C(Cl)Cl.O1CCCC1 | C-C Coupling | Suzuki coupling with boronic acids | 321c3e72a16fdf6182f73085de3887109bfe6c412c5fe044d103e8cc0d412652 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1OCC2Cc3cc(-c4ccccc4)ccc3N12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | null | null | null | null | (±) (1S,9aS/1R,9aR) N-[(7-Bromo-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 24, 129 mg) is dissolved in tetrahydrofuran (1 ml). To this mixture palladium tetrakis(triphenylphosphine) (22 mg), phenylboronic acid (61 mg) and aqueous sodium carbonate (2M, 0.45 ml) is added. The mixture is w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CC1COCN21.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC1COCN21 | c1ccccc1.c1ccc2c(c1)CC1COCN21 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C(Cl)Cl.O1CCCC1 | null | null | CC(=O)NCC1OC(=O)N2c3ccc(Br)cc3CC12.OB(O)c1ccccc1>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Pd].C(Cl)Cl.O1CCCC1>CC(=O)NCC1OC(=O)N2c3ccc(-c4ccccc4)cc3CC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-344b5d26f989476db51adec38886cea4 | CC(=O)NC[C@@H]1OC(=O)N2c3ccc(C(=O)CCl)cc3C[C@@H]12.[N-]=[N+]=[N-]>>CC(=O)NC[C@@H]1OC(=O)N2c3ccc(C(=O)CN=[N+]=[N-])cc3C[C@@H]12 | ClCC(=O)C1=CC=2C[C@@H]3N(C2C=C1)C(O[C@H]3CNC(C)=O)=O.[N-]=[N+]=[N-].[Na+].CC(=O)C>>N(=[N+]=[N-])CC(=O)C1=CC=2C[C@@H]3N(C2C=C1)C(O[C@H]3CNC(C)=O)=O | Cl[CH2:17][C:15]([c:14]1[cH:13][cH:12][c:11]2[c:22]([cH:21]1)[CH2:23][C@H:24]1[C@H:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:7][C:8](=[O:9])[N:10]21)=[O:16].[N-:18]=[N+:19]=[N-:20]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@@H:6]1[O:7][C:8](=[O:9])[N:10]2[c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[CH2:17][N:18]=[N+:19]=[N-:20]... | CC(=O)NC[C@@H]1OC(=O)N2c3ccc(C(=O)CCl)cc3C[C@@H]12.[N-]=[N+]=[N-] | CC(=O)NC[C@@H]1OC(=O)N2c3ccc(C(=O)CN=[N+]=[N-])cc3C[C@@H]12 | null | null | C(Cl)Cl.CO.CO.C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 7fe919211b759a1428a74cb1057710661d1d522f092678548e8299963d0e0365 | f47c52494d5e4df5ea8fcd9d0881525b7662fe98ccef006a42d77c12f4514758 | O=C1OC[C@@H]2Cc3ccccc3N12 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | A mixture of (1S,9aS) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 48, 43 mg) and sodium azide (82 mg) are stirred in aqueous tetrahydrofuran (66%) for 3 days. Acetone (1 ml) is added and the mixture was heated in an oil bath (38°-50°) for 8 hours then concentrated to a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Azide | null | null | c1ccc2c(c1)C[C@H]1COCN21 | Other | C(Cl)Cl.CO.CO.C(C)(=O)OCC.O1CCCC1 | null | null | CC(=O)NC[C@@H]1OC(=O)N2c3ccc(C(=O)CCl)cc3C[C@@H]12.[N-]=[N+]=[N-]>C(Cl)Cl.CO.CO.C(C)(=O)OCC.O1CCCC1>CC(=O)NC[C@@H]1OC(=O)N2c3ccc(C(=O)CN=[N+]=[N-])cc3C[C@@H]12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4f75d89850dd4de3a07f2755539ba444 | CCOC(=O)CCc1cc(=O)oc2cc(OC)ccc12>>CCOC(=O)CCc1cc(=O)oc2cc(O)ccc12 | C(=O)(OCC)CCC1=CC(OC2=C1C=CC(=C2)OC)=O.[Al+3].[Cl-].[Cl-].[Cl-].CCS>>C(=O)(OCC)CCC1=CC(OC2=C1C=CC(=C2)O)=O | C[O:16][c:15]1[cH:14][c:13]2[o:12][c:10](=[O:11])[cH:9][c:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:19]2[cH:18][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][c:10](=[O:11])[o:12][c:13]2[cH:14][c:15]([OH:16])[cH:17][cH:18][c:19]12 | CCOC(=O)CCc1cc(=O)oc2cc(OC)ccc12 | CCOC(=O)CCc1cc(=O)oc2cc(O)ccc12 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccc2ccccc2o1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#8;a:6]>>[#8;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 27.1 | [{"value": 27.0, "product": "C(=O)(OCC)CCC1=CC(OC2=C1C=CC(=C2)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.1, "product": "C(=O)(OCC)CCC1=CC(OC2=C1C=CC(=C2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a suspension of 726 mg (5.4 mmol) of AlCl3 in 10 mL of dichloromethane at 0° C. was added 4 mL of EtSH. The suspension became a clear solution within seconds. Then, 298 mg (1.08 mmol) of 3 in 4 mL of dichloromethane was added, turning the yellow solution red in color. The ice bath was removed, and the reaction stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2cccoc2c1 | Other | ClCCl | null | 3 | CCOC(=O)CCc1cc(=O)oc2cc(OC)ccc12>ClCCl>CCOC(=O)CCc1cc(=O)oc2cc(O)ccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5286c593126f48fab83604898c4bbbb3 | CC(C)c1ccccc1.[Cl-].[Zr+4]>>[Cl-].[Zr+2].c1cc[cH-]c1.c1cc[cH-]c1 | [Cl-].[Cl-].[Cl-].[Cl-].[Zr+4].C1(=CC=CC=C1)C(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[Al]>>[Cl-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Zr+2] | [CH3:4][CH:9]([CH3:10])[c:12]1[cH:5][cH:6][cH:7][cH:8][cH:11]1.[Cl-:1].[Zr+4:3]>>[Cl-:1].[Zr+2:3].[cH:4]1[cH:5][cH:6][cH-:7][cH:8]1.[cH:9]1[cH:10][cH:11][cH-:12][cH:13]1 | CC(C)c1ccccc1.[Cl-].[Zr+4] | [Cl-].[Zr+2].c1cc[cH-]c1.c1cc[cH-]c1 | null | [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] | ClCCl.Cl | C-C Coupling | OtherReaction | e0e1b7c2412674352fec06e7469b33e092804fd3084b44106778893e3e685e83 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1cc[cH-]c1.c1cc[cH-]c1 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[cH;D2;+0:9]:1.[Zr+4;H0;D0:10]>>[Zr+2;H0;D0:10].[c:8]1:[cH-;D2:7]:[cH;D2;+0:6]:[cH;D2;+0:3]:[cH;D2;+0:9]:1.[c:11]1:[cH-;D2:4]:[cH;D2;+0:5]:[cH;D2;+0:1]:[cH;D2;+0:2]:1 | 118.6 | [{"value": 118.6, "product": "[Cl-].[Cl-].[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Zr+2]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 1.5 | HOUR | 17.5 g (0.075 mol) of zirconium tetrachloride are added at 60° C. under nitrogen over 30 minutes to a stirred mixture of 129.7 g (1.265 mol) of cumene, 27.9 g (0.15 mol) of ferrocene, 26.6 g (0.199 mol) of aluminium chloride and 0.7 g (0.025 mol) of aluminium powder. The reaction mixture is heated and then stirred for ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | c1cc[cH-]c1.c1cc[cH-]c1 | c1cc[cH-]c1.c1cc[cH-]c1 | Other | [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].ClCCl.Cl | 110 | 1.5 | CC(C)c1ccccc1.[Cl-].[Zr+4]>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].ClCCl.Cl>[Cl-].[Zr+2].c1cc[cH-]c1.c1cc[cH-]c1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-252f1c823e9e43e99c8d940165851311 | CC(C)c1ccccc1.[Cl-]>>[C-]1=CC=CC1.[C-]1=CC=CC1.[Cl-] | [Cl-].[Cl-].[Cl-].[Cl-].[Hf+4].C1(=CC=CC=C1)C(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[Al]>>C1C=CC=[C-]1.C1C=CC=[C-]1.[Cl-].[Cl-].[Hf+4] | [CH3:1][CH:7]([c:6]1[cH:5][cH:4][cH:3][cH:2][cH:10]1)[CH3:8].[Cl-:12]>>[C-:1]1=[CH:2][CH:3]=[CH:4][CH2:5]1.[C-:6]1=[CH:7][CH:8]=[CH:9][CH2:10]1.[Cl-:12] | CC(C)c1ccccc1.[Cl-] | [C-]1=CC=CC1.[C-]1=CC=CC1.[Cl-] | null | [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] | null | Functional Group Addition | OtherReaction | 5300820edca2388259b8d47deae875ec2bb6a38cd2991977a769a346b406a0ba | 69ece274e0104838fc859dee2bcf07ab566679ccfd515c3388e20b73f1d85347 | [C-]1=CC=CC1.[C-]1=CC=CC1 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1>>[C-;H0;D2:1]1=[CH;D2;+0:6]-[CH;D2;+0:7]=[CH;D2;+0:8]-[CH2;D2;+0:9]-1.[C-;H0;D2:4]1=[CH;D2;+0:2]-[CH;D2;+0:3]=[C:10]-[CH2;D2;+0:5]-1 | 137.6 | [{"value": 68.6, "product": "C1C=CC=[C-]1.C1C=CC=[C-]1.[Cl-].[Cl-].[Hf+4]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 137.6, "product": "C1C=CC=[C-]1.C1C=CC=[C-]1.[Cl-].[Cl-].[Hf+4]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In accordance with the procedure of Example 5, 4.3 g (0.0134 mol) of hafnium tetrachloride are added at 55° C. under nitrogen over 30 minutes to a stirred mixture of 56 g of cumene, 5 g (0.027 mol) of ferrocene, 4.8 g (0.0358 mol) of aluminium chloride and 0.12 g (0.0045 mol) of aluminium powder. Working up is effected... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | [C-]1=CC=CC1.[C-]1=CC=CC1 | [C-]1=CC=CC1.[C-]1=CC=CC1 | Other | [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2] | null | null | CC(C)c1ccccc1.[Cl-]>[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2]>[C-]1=CC=CC1.[C-]1=CC=CC1.[Cl-] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6e509896da094dc58fef5e22f2f94349 | [Fe+2].c1cc[cH-]c1>>[Fe+][CH]1C=CC=C1 | [CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Al+3].[Cl-].[Cl-].[Cl-].C1(=CC(=CC(=C1)C)C)C>>C1(=CC(=CC(=C1)C)C)C.C1(C=CC=C1)[Fe+] | [Fe+2:10].[cH-:11]1[cH:12][cH:13][cH:14][cH:15]1>>[Fe+:10][CH:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1 | [Fe+2].c1cc[cH-]c1 | [Fe+][CH]1C=CC=C1 | null | [Cl-].[Cl-].[Cl-].[Cl-].[Zr+4] | null | Miscellaneous | OtherReaction | 3e7d8a9e6b3a21f254f38900e33c5d2b42d306e4fe23616cd746c94c42dbd1ca | 6bd737fa4af3d355e9cf0582097233ad10bd40cdbf75d943023728a3aa172d9b | C1=CCC=C1 | [Fe+2;H0;D0:1].[cH-;D2:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:1>>[Fe+;H0;D1:1]-[CH;D3;+0:2]1-[CH;D2;+0:3]=[CH;D2;+0:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1 | null | [] | null | null | null | null | In accordance with the procedure of Example 4, 10 g (0.043 mol) of ZrCl4 are added at 60° C. under argon over the course of 1 hour and 10 minutes to a stirred mixture of 60 ml of mesitylene, 8 g (0.043 mol) of ferrocene and 5.7 g (0.043 mol) of sublimed AlCl3. Working up is effected as in Example 4, affording 20.1 g (8... | 10.6084/m9.figshare.5104873.v1 | null | null | Conjugated diene | c1cc[cH-]c1 | C1=CCC=C1 | C1=CCC=C1 | null | [Cl-].[Cl-].[Cl-].[Cl-].[Zr+4] | null | null | [Fe+2].c1cc[cH-]c1>[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Fe+][CH]1C=CC=C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-86fb1dcff3c742f79157360a3f708f8a | CCOP(=O)(COCCOC(C)=O)OCC>>CCOP(=O)(COCCO)OCC | C(C)(=O)OCCOCP(OCC)(OCC)=O.[O-]CC.[Na+]>>OCCOCP(OCC)(OCC)=O | CC(=O)[O:10][CH2:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][CH2:9][OH:10])[O:11][CH2:12][CH3:13] | CCOP(=O)(COCCOC(C)=O)OCC | CCOP(=O)(COCCO)OCC | null | null | C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 70 | [{"value": 70.0, "product": "OCCOCP(OCC)(OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of diethyl 2-acetoxyethoxymethylphosphonate* (16 g, 63 mmol) in absolute ethanol (150 ml), was added 0.5M sodium ethoxide (12.19 ml). After standing at ambient temperature overnight, 1R-120H resin was added until pH 6.5 was reached. The solution was filtered immediately, the resin washed with ethanol and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | HO- | C(C)O | null | 8 | CCOP(=O)(COCCOC(C)=O)OCC>C(C)O>CCOP(=O)(COCCO)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-da5eb9e19a5b48feb45235011949984d | CCOP(=O)(COCCONc1ncnc(Cl)c1NC=O)OCC>>CCOP(=O)(COCCOn1cnc2c(Cl)ncnc21)OCC | ClC1=NC=NC(=C1NC=O)NOCCOCP(=O)(OCC)OCC>>ClC1=C2N=CN(C2=NC=N1)OCCOCP(=O)(OCC)OCC | O=[CH:12][NH:13][c:14]1[c:15]([Cl:16])[n:17][cH:18][n:19][c:20]1[NH:11][O:10][CH2:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:21][CH2:22][CH3:23]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][CH2:9][O:10][n:11]1[cH:12][n:13][c:14]2[c:15]([Cl:16])[n:17][cH:18][n:19][c:20]12)[O:21][CH2:22][CH3:23] | CCOP(=O)(COCCONc1ncnc(Cl)c1NC=O)OCC | CCOP(=O)(COCCOn1cnc2c(Cl)ncnc21)OCC | null | null | C(C)(=O)OC(OCC)OCC | Aromatic Heterocycle Formation | OtherReaction | 8965b507f2073429513b0b0631d4e3660f98191aaf94a371276afd539bcb7aed | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ncc2nc[nH]c2n1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[c:3]1:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[NH;D2;+0:10]-[#8:11]-[C:12]>>[C:12]-[#8:11]-[n;H0;D3;+0:10]1:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[c:3]2:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | 94 | [{"value": 94.0, "product": "ClC1=C2N=CN(C2=NC=N1)OCCOCP(=O)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "ClC1=C2N=CN(C2=NC=N1)OCCOCP(=O)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A solution of 4-chloro-6-[2-(diethoxyphosphorylmethoxy)ethoxyamino]-5-formamidopyrimidine (2.4 g, 6.3 mmol) in diethoxymethyl acetate (10 ml) was heated at 120° C. for 45 minutes. After cooling to ambient temperature, the solvent was removed under reduced pressure. The residue was dissolved in methanol (15 ml) and 0.88... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1cncnc1 | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | HO- | C(C)(=O)OC(OCC)OCC | null | 0.25 | CCOP(=O)(COCCONc1ncnc(Cl)c1NC=O)OCC>C(C)(=O)OC(OCC)OCC>CCOP(=O)(COCCOn1cnc2c(Cl)ncnc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-97703c536bb449538d3e957266c1c6f1 | CCOP(=O)(COCCONc1nc(NC=O)nc(Cl)c1NC=O)OCC>>CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC | ClC1=NC(=NC(=C1NC=O)NOCCOCP(=O)(OCC)OCC)NC=O>>ClC1=C2N=CN(C2=NC(=N1)NC=O)OCCOCP(=O)(OCC)OCC | O=[CH:12][NH:13][c:14]1[c:15]([Cl:16])[n:17][c:18]([NH:19][CH:20]=[O:21])[n:22][c:23]1[NH:11][O:10][CH2:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][CH2:9][O:10][n:11]1[cH:12][n:13][c:14]2[c:15]([Cl:16])[n:17][c:18]([NH:19][CH:20]=[O... | CCOP(=O)(COCCONc1nc(NC=O)nc(Cl)c1NC=O)OCC | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC | null | null | C(C)(=O)OC(OCC)OCC | Aromatic Heterocycle Formation | OtherReaction | 770e93dbecceb1c0b4e1c63279b237f8a480eec443f222f24f87a9f0fa95fbca | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ncc2nc[nH]c2n1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[c:3]1:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[NH;D2;+0:10]-[#8:11]-[C:12]>>[C:12]-[#8:11]-[n;H0;D3;+0:10]1:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[c:3]2:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | 90 | [{"value": 90.0, "product": "ClC1=C2N=CN(C2=NC(=N1)NC=O)OCCOCP(=O)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "ClC1=C2N=CN(C2=NC(=N1)NC=O)OCCOCP(=O)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-chloro-6-[2-(diethoxyphosphorylmethoxy) ethoxyamino]-2,5-diformamidopyrimidine (2.8 g, 6.6 mmol) in diethoxymethyl acetate (20 ml) was heated at 120° C. for 2 hours. After cooling to ambient temperature, excess solvent was removed under reduced pressure, the residue dissolved in methanol (20 ml) and 0.8... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1cncnc1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HO- | C(C)(=O)OC(OCC)OCC | null | 1 | CCOP(=O)(COCCONc1nc(NC=O)nc(Cl)c1NC=O)OCC>C(C)(=O)OC(OCC)OCC>CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1159650d17344e7fa82a836be2dcb965 | C=O.CCOP(OCC)OCC.OC(COCc1ccccc1)COCc1ccccc1>>CCOP(=O)(COC(COCc1ccccc1)COCc1ccccc1)OCC | C(C1=CC=CC=C1)OCC(COCC1=CC=CC=C1)O.C=O.P(OCC)(OCC)OCC>>C(C1=CC=CC=C1)OCC(OCP(OCC)(OCC)=O)COCC1=CC=CC=C1 | O=[CH2:6].CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:27][CH2:28][CH3:29].[OH:7][CH:8]([CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH2:18][O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][... | C=O.CCOP(OCC)OCC.OC(COCc1ccccc1)COCc1ccccc1 | CCOP(=O)(COC(COCc1ccccc1)COCc1ccccc1)OCC | null | null | ClCCl.C(C)(=O)OCC | Protection | OtherReaction | 763efef778fa276c77d646fede2364047aa08effbaa695dcc485056c023e04b8 | 81281c7e22196131efc3b1b9a66ac4c58bcf274372e0b3b48528b083a52505a9 | c1ccc(COCCCOCc2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[P;H0;D3;+0:2](-[#8:3]-[C:4])-[#8:5]-[C:6].O=[CH2;D1;+0:7].[C:8]-[C:9](-[C:10])-[OH;D1;+0:11]>>[C:8]-[C:9](-[C:10])-[O;H0;D2;+0:11]-[CH2;D2;+0:7]-[P;H0;D4;+0:2](=[O;H0;D1;+0:1])(-[#8:3]-[C:4])-[#8:5]-[C:6] | null | [] | 140 | CELSIUS | null | null | Dry HCl gas was bubbled through an ice-cooled solution of 1,3-dibenzyloxypropan-2-ol (25 g, 0.092 mol) and paraformaldehyde (2.75 g, 0.092 mol) in dry dichloromethane (100 ml) for 1 hour. The resulting solution was dried (MgSO4) and evaporated to dryness to leave an oil. Triethyl phosphite (15.7 ml, 0.092 mol) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | ClCCl.C(C)(=O)OCC | 140 | null | C=O.CCOP(OCC)OCC.OC(COCc1ccccc1)COCc1ccccc1>ClCCl.C(C)(=O)OCC>CCOP(=O)(COC(COCc1ccccc1)COCc1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-79f3846e5c26492db5b28dd5230190e2 | CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(Cl)ncnc21)OCC.N>>CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(N)ncnc21)OCC | C(C1=CC=CC=C1)OCC(CON1C2=NC=NC(=C2N=C1)Cl)OCP(=O)(OCC)OCC.N>>C(C1=CC=CC=C1)OCC(CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(OCC)OCC | Cl[c:24]1[c:23]2[n:22][cH:21][n:20]([O:19][CH2:18][CH:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:30][CH2:31][CH3:32])[CH2:9][O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:29]2[n:28][cH:27][n:26]1.[NH3:25]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:... | CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(Cl)ncnc21)OCC.N | CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(N)ncnc21)OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d1ce4daf8ecb5816a05bfd6b5c1acf9fbd8b669f52cd7e645f544d6a4a7dba23 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(COCCCOn2cnc3cncnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[#8:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[#8:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | 64 | [{"value": 64.0, "product": "C(C1=CC=CC=C1)OCC(CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-chloropurine (570 mg, 1.18 mmol) in ethanolic ammonia (10 ml) was heated in a sealed vessel at 110° C. for 2 hours. After cooling to ambient temperature, the solvent was evaporated and the residue obtained chromatographed on silica (dichloromethane/me... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ncnc2nc[nH]c12 | c1ncnc2[nH]cnc12 | c1ccccc1.c1ncnc2[nH]cnc12 | HCl | null | null | null | CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(Cl)ncnc21)OCC.N>>CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(N)ncnc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ca0089c60afa41788d06a4e5994a6587 | CCOP(=O)(COC(COCc1ccccc1)CONc1nc(NC=O)nc(Cl)c1NC=O)OCC>>CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(Cl)nc(NC=O)nc21)OCC | C(C1=CC=CC=C1)OCC(CONC1=C(C(=NC(=N1)NC=O)Cl)NC=O)OCP(=O)(OCC)OCC>>C(C1=CC=CC=C1)OCC(CON1C2=NC(=NC(=C2N=C1)Cl)NC=O)OCP(=O)(OCC)OCC | O=[CH:21][NH:22][c:23]1[c:24]([Cl:25])[n:26][c:27]([NH:28][CH:29]=[O:30])[n:31][c:32]1[NH:20][O:19][CH2:18][CH:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:33][CH2:34][CH3:35])[CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][CH2:1... | CCOP(=O)(COC(COCc1ccccc1)CONc1nc(NC=O)nc(Cl)c1NC=O)OCC | CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(Cl)nc(NC=O)nc21)OCC | null | null | C(C)(=O)OC(OCC)OCC | Aromatic Heterocycle Formation | OtherReaction | 770e93dbecceb1c0b4e1c63279b237f8a480eec443f222f24f87a9f0fa95fbca | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ccc(COCCCOn2cnc3cncnc32)cc1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[c:3]1:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:1-[NH;D2;+0:10]-[#8:11]-[C:12]>>[C:12]-[#8:11]-[n;H0;D3;+0:10]1:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[c:3]2:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1 | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)OCC(CON1C2=NC(=NC(=C2N=C1)Cl)NC=O)OCP(=O)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.4, "product": "C(C1=CC=CC=C1)OCC(CON1C2=NC(=NC(=C2N=C1)Cl)NC=O)OCP(=O)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 6-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxyamino]-4-chloro-2,5-diformamidopyrimidine (760 mg, 1.4 mmol) in diethoxymethyl acetate (2 ml) was stirred and heated in an oil bath at 120° C. for 2 hours. After cooling to ambient temperature, the solvent was evaporated and the residue dissolved in metha... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1cncnc1 | c1ncc2nc[nH]c2n1 | c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | C(C)(=O)OC(OCC)OCC | 120 | null | CCOP(=O)(COC(COCc1ccccc1)CONc1nc(NC=O)nc(Cl)c1NC=O)OCC>C(C)(=O)OC(OCC)OCC>CCOP(=O)(COC(COCc1ccccc1)COn1cnc2c(Cl)nc(NC=O)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1ecd3089eefd43c196a7041c766f44e5 | CCOP(=O)(COC(CON)COC(C)=O)OCC.O=CNc1c(Cl)ncnc1Cl>>CCOP(=O)(COC(CONc1ncnc(Cl)c1NC=O)COC(C)=O)OCC | ClC1=NC=NC(=C1NC=O)Cl.C(C)(=O)OCC(OCP(OCC)(OCC)=O)CON.C(C)N(CC)CC>>C(C)(=O)OCC(CONC1=C(C(=NC=N1)Cl)NC=O)OCP(=O)(OCC)OCC | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][NH2:11])[CH2:22][O:23][C:24]([CH3:25])=[O:26])[O:27][CH2:28][CH3:29].Cl[c:12]1[n:13][cH:14][n:15][c:16]([Cl:17])[c:18]1[NH:19][CH:20]=[O:21]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][NH:11][c:12]1[n:13][cH:14][n:15][c:16]([Cl:17]... | CCOP(=O)(COC(CON)COC(C)=O)OCC.O=CNc1c(Cl)ncnc1Cl | CCOP(=O)(COC(CONc1ncnc(Cl)c1NC=O)COC(C)=O)OCC | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[#7:8]-[C:9]=[O;D1;H0:10].[C:11]-[#8:12]-[NH2;D1;+0:13]>>[C:11]-[#8:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[#7:8]-[C:9]=[O;D1;H0:10] | 60 | [{"value": 60.0, "product": "C(C)(=O)OCC(CONC1=C(C(=NC=N1)Cl)NC=O)OCP(=O)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C(C)(=O)OCC(CONC1=C(C(=NC=N1)Cl)NC=O)OCP(=O)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 4,6-dichloro-5-formamidopyrimidine (0.77 g, 4.0 mmol), diethyl [2-acetoxy-1-(aminooxymethyl)ethoxy]methylphosphonate (1.2 g, 4.0 mmol) and triethylamine (0.82 ml, 6 mmol) in dry dioxan (20 ml) was heated at 100° C. for 2 hours. The reaction mixture was cooled, filtered, and the filtrate evaporated to leave... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | O1CCOCC1 | 100 | null | CCOP(=O)(COC(CON)COC(C)=O)OCC.O=CNc1c(Cl)ncnc1Cl>O1CCOCC1>CCOP(=O)(COC(CONc1ncnc(Cl)c1NC=O)COC(C)=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5fc21e67a610459991f0bba4b51294ed | CCOP(=O)(COC(CON)COC(C)=O)OCC.O=CNc1nc(Cl)c(NC=O)c(Cl)n1>>CCOP(=O)(COC(CONc1nc(NC=O)nc(Cl)c1NC=O)COC(C)=O)OCC | ClC1=NC(=NC(=C1NC=O)Cl)NC=O.C(C)(=O)OCC(OCP(OCC)(OCC)=O)CON.C(C)N(CC)CC>>C(C)(=O)OCC(CONC1=C(C(=NC(=N1)NC=O)Cl)NC=O)OCP(=O)(OCC)OCC | [CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][NH2:11])[CH2:25][O:26][C:27]([CH3:28])=[O:29])[O:30][CH2:31][CH3:32].Cl[c:12]1[n:13][c:14]([NH:15][CH:16]=[O:17])[n:18][c:19]([Cl:20])[c:21]1[NH:22][CH:23]=[O:24]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][O:10][NH:11][c:12]1[n:13][c:14... | CCOP(=O)(COC(CON)COC(C)=O)OCC.O=CNc1nc(Cl)c(NC=O)c(Cl)n1 | CCOP(=O)(COC(CONc1nc(NC=O)nc(Cl)c1NC=O)COC(C)=O)OCC | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[#7:8]-[C:9]=[O;D1;H0:10].[C:11]-[#8:12]-[NH2;D1;+0:13]>>[C:11]-[#8:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[#7:8]-[C:9]=[O;D1;H0:10] | 81.4 | [{"value": 80.0, "product": "C(C)(=O)OCC(CONC1=C(C(=NC(=N1)NC=O)Cl)NC=O)OCP(=O)(OCC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "C(C)(=O)OCC(CONC1=C(C(=NC(=N1)NC=O)Cl)NC=O)OCP(=O)(OCC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of 4,6-dichloro-2,5-diformamidopyrimidine (0.475 mg, 2 mmol), diethyl [2-acetoxy-1-(aminooxymethyl)ethoxy)methylphosphonate (0.60 mg, 2 mmol) and triethylamine (0.54 ml, 4 mmol) in dry dioxan (20 ml) was heated at 120° C. for 5 hours. The reaction mixture was cooled to ambient temperature, filtered, and the f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | O1CCOCC1 | 120 | null | CCOP(=O)(COC(CON)COC(C)=O)OCC.O=CNc1nc(Cl)c(NC=O)c(Cl)n1>O1CCOCC1>CCOP(=O)(COC(CONc1nc(NC=O)nc(Cl)c1NC=O)COC(C)=O)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b7ee7fbacb394ae7a8be509b810a5cae | Clc1ncnc2c1ncn2OCc1ccccc1.N>>Nc1ncnc2c1ncn2OCc1ccccc1 | [K+].[Br-].C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)Cl.N>>C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)N | Cl[c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[NH3:1]>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Clc1ncnc2c1ncn2OCc1ccccc1.N | Nc1ncnc2c1ncn2OCc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f878bd277b2108dc3fd65f78056269ecc87ed81e1d894e049e2ae4d9d931682f | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(COn2cnc3cncnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[#8:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[#8:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | A solution of 9-benzyloxy-6-chloropurine (38.4 g; 0.147 mmol) in ethanol (300 ml) saturated with ammonia was heated at 100° C. in an autoclave for 16 hours. After cooling the suspension was evaporated to dryness and the residue partitioned between chloroform (750 ml) and water (500 ml). The separated aqueous phase was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ncnc2nc[nH]c12 | c1ncnc2nc[nH]c12 | c1ncnc2nc[nH]c12.c1ccccc1 | HCl | C(C)O | null | null | Clc1ncnc2c1ncn2OCc1ccccc1.N>C(C)O>Nc1ncnc2c1ncn2OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9d6d039efa9945a3beb94d8cc151e292 | Nc1ncnc2c1ncn2OCc1ccccc1.O=C(Cl)c1ccccc1C(=O)Cl>>O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1 | C(C=1C(C(=O)Cl)=CC=CC1)(=O)Cl.C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)N.C(C)N(CC)CC>>C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O | [NH2:11][c:12]1[n:13][cH:14][n:15][c:16]2[c:17]1[n:18][cH:19][n:20]2[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9](Cl)=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[c:12]1[n:13][cH:14][n:15][c:16]2[c:17]1[n:18][cH:19][n:... | Nc1ncnc2c1ncn2OCc1ccccc1.O=C(Cl)c1ccccc1C(=O)Cl | O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1 | null | CN(C1=CC=NC=C1)C | O1CCCC1 | Acylation | OtherReaction | 5627546af56be458f2fe7e00b590da2a122b3685c398c18b11256acd41538480 | 17c24b4ae3ed71a7380cf4f231fdd687ffeb87512c3dc2a622f01c3349bbcbdf | O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](-Cl)=[O;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]2:[#7;a:15]:[c:16]:[#7;a:17]:[c:18]:1:2>>[O;D1;H0:7]=[C;H0;D3;+0:6]1-[N;H0;D3;+0:9](-[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]3:[#7;a:15]:[c:16]:[#7;a:17]:[c:18]:2:3)-[C;H0;... | 49 | [{"value": 49.0, "product": "C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Phthaloyl dichloride (13.35 g; 92.2 mmol) was added to a cooled solution of 9-benzyloxyadenine (14.9 g, 61.5 mmol), 4-dimethylaminopyridine (1.5 g, 12.3 mmol) and triethylamine (25.7 ml, 184.4 mmol) in tetrahydrofuran (200 ml). After 1 hour at room temperature the solvent was removed under reduced pressure and the resi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ncnc2nc[nH]c12.c1ccccc1 | HCl | CN(C1=CC=NC=C1)C.O1CCCC1 | null | null | Nc1ncnc2c1ncn2OCc1ccccc1.O=C(Cl)c1ccccc1C(=O)Cl>CN(C1=CC=NC=C1)C.O1CCCC1>O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bcb1f28502a14261b19c5dc4802361c3 | O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1>>O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2O | C(C1=CC=CC=C1)ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O.C(C)O>>ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O | c1ccc(C[O:21][n:20]2[c:16]3[n:15][cH:14][n:13][c:12]([N:11]4[C:2](=[O:1])[c:3]5[cH:4][cH:5][cH:6][cH:7][c:8]5[C:9]4=[O:10])[c:17]3[n:18][cH:19]2)cc1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[c:12]1[n:13][cH:14][n:15][c:16]2[c:17]1[n:18][cH:19][n:20]2[OH:21] | O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1 | O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2O | null | [Pd] | O1CCCC1 | Deprotection | OtherReaction | 94fa5e5ed4a5b32c4aba0dd3c8151bfdd08491d1bc6453e9fd01d7dc3e51cd0f | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=C1c2ccccc2C(=O)N1c1ncnc2[nH]cnc12 | [#7;a:1]:[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1>>[#7;a:1]:[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[OH;D1;+0:7] | 83.5 | [{"value": 83.0, "product": "ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.5, "product": "ON1C2=NC=NC(=C2N=C1)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 1 | HOUR | A mixture of 9-benzyloxy-6-phthalimidopurine (11.0 g, 29.5 mmol), 10% palladium on charcoal (2.2 g), ethanol (300 ml) and tetrahydrofuran (500 ml) was stirred at 25° C. for 1 hour under an atmosphere of hydrogen. The suspension was then filtered and the catalyst washed with ethanol. The filtrate was evaporated under re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | null | c1ccc2c(c1)C[NH]C2.c1ncnc2nc[nH]c12 | Other | [Pd].O1CCCC1 | 25 | 1 | O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2OCc1ccccc1>[Pd].O1CCCC1>O=C1c2ccccc2C(=O)N1c1ncnc2c1ncn2O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-44cf70cb0643481db455beee7bccf37f | NOCc1ccccc1.O=CNc1nc(Cl)c(NC=O)c(Cl)n1>>O=CNc1nc(Cl)c(NC=O)c(NOCc2ccccc2)n1 | ClC1=NC(=NC(=C1NC=O)Cl)NC=O.C(C1=CC=CC=C1)ON.C(C)N(CC)CC>>C(C1=CC=CC=C1)ONC1=C(C(=NC(=N1)NC=O)Cl)NC=O | [NH2:13][O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.Cl[c:12]1[c:8]([NH:9][CH:10]=[O:11])[c:6]([Cl:7])[n:5][c:4]([NH:3][CH:2]=[O:1])[n:22]1>>[O:1]=[CH:2][NH:3][c:4]1[n:5][c:6]([Cl:7])[c:8]([NH:9][CH:10]=[O:11])[c:12]([NH:13][O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22]1 | NOCc1ccccc1.O=CNc1nc(Cl)c(NC=O)c(Cl)n1 | O=CNc1nc(Cl)c(NC=O)c(NOCc2ccccc2)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CONc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]-[C:5]=[O;D1;H0:6]):[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:10]:1-[#7:11]-[C:12]=[O;D1;H0:13].[C:14]-[#8:15]-[NH2;D1;+0:16]>>[C:14]-[#8:15]-[NH;D2;+0:16]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]-[C:5]=[O;D1;H0:6]):[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[c:10]:1-[#7:11]-[C:12]=[O;D1;H0:13] | 46.1 | [{"value": 46.0, "product": "C(C1=CC=CC=C1)ONC1=C(C(=NC(=N1)NC=O)Cl)NC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "C(C1=CC=CC=C1)ONC1=C(C(=NC(=N1)NC=O)Cl)NC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | A mixture of 4,6-dichloro-2,5-diformamido-pyrimidine (1.9 g, 8.09 mmol), benzyloxyamine (1 g, 8.13 mmol), triethylamine (2 ml) and dioxan (20 ml) was stirred at 100° C. for 1 hour. The cooled reaction mixture was filtered and the precipitate collected and washed with dioxan (2×5 ml). The filtrate and washings were comb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | O1CCOCC1 | 100 | 1 | NOCc1ccccc1.O=CNc1nc(Cl)c(NC=O)c(Cl)n1>O1CCOCC1>O=CNc1nc(Cl)c(NC=O)c(NOCc2ccccc2)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3e75075e6e304267be1415e6af320c90 | O=CNc1nc(Cl)c(NC=O)c(NOCc2ccccc2)n1>>O=CNc1nc(Cl)c2ncn(OCc3ccccc3)c2n1 | C(C1=CC=CC=C1)ONC1=C(C(=NC(=N1)NC=O)Cl)NC=O>>C(C1=CC=CC=C1)ON1C2=NC(=NC(=C2N=C1)Cl)NC=O | O=[CH:10][NH:9][c:8]1[c:6]([Cl:7])[n:5][c:4]([NH:3][CH:2]=[O:1])[n:21][c:20]1[NH:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[CH:2][NH:3][c:4]1[n:5][c:6]([Cl:7])[c:8]2[n:9][cH:10][n:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]2[n:21]1 | O=CNc1nc(Cl)c(NC=O)c(NOCc2ccccc2)n1 | O=CNc1nc(Cl)c2ncn(OCc3ccccc3)c2n1 | null | null | C(C)(=O)OC(OCC)OCC | Aromatic Heterocycle Formation | OtherReaction | 86abaf3faa18eba7791224efe6cc43a66f7a73e51a722a71d0abd12a40c2c2cd | 71fdeda1d5481ba7466e825735d29b5ffca597c091e9548c43a80a0aea31b8a0 | c1ccc(COn2cnc3cncnc32)cc1 | O=[CH;D2;+0:1]-[NH;D2;+0:2]-[c:3]1:[c:4](-[NH;D2;+0:5]-[#8:6]-[C:7]):[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[Cl;D1;H0:12]>>[C:7]-[#8:6]-[n;H0;D3;+0:5]1:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[c:3]2:[c:4]:1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2-[Cl;D1;H0:12] | 62 | [{"value": 62.0, "product": "C(C1=CC=CC=C1)ON1C2=NC(=NC(=C2N=C1)Cl)NC=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.8, "product": "C(C1=CC=CC=C1)ON1C2=NC(=NC(=C2N=C1)Cl)NC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 6-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidine (1.2 g, 3.73 mmol) and diethoxymethyl acetate (20 ml) was stirred at 120° C. for 2.5 hours, cooled and evaporated under reduced pressure. A solution of the residue in methanol (20 ml) and 0.880 ammonia (2 ml) was stirred at 20° C. for 1 hour, the solvent removed under... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Secondary amine | null | c1cncnc1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.c1ccccc1 | HO- | C(C)(=O)OC(OCC)OCC | 20 | 1 | O=CNc1nc(Cl)c(NC=O)c(NOCc2ccccc2)n1>C(C)(=O)OC(OCC)OCC>O=CNc1nc(Cl)c2ncn(OCc3ccccc3)c2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-77f6d3fcdd68490a95d4914b5d82aeb2 | C[O-].O=CNc1nc(Cl)c2ncn(OCc3ccccc3)c2n1>>COc1nc(N)nc2c1ncn2OCc1ccccc1 | C(C1=CC=CC=C1)ON1C2=NC(=NC(=C2N=C1)Cl)NC=O.C[O-].[Na+].C(C)(=O)O>>NC1=NC(=C2N=CN(C2=N1)OCC1=CC=CC=C1)OC | [CH3:1][O-:2].O=C[NH:6][c:5]1[n:4][c:3](Cl)[c:9]2[c:8]([n:7]1)[n:12]([O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[cH:11][n:10]2>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:7][c:8]2[c:9]1[n:10][cH:11][n:12]2[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | C[O-].O=CNc1nc(Cl)c2ncn(OCc3ccccc3)c2n1 | COc1nc(N)nc2c1ncn2OCc1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 27fb547e1738ce7b397c632bacc2774bc12b7d69b21c786ce8e559700728935a | e57780d4790e25e68acbbbe4f1c7358f65a7d1bfb61e3b5833651a99a8d19025 | c1ccc(COn2cnc3cncnc32)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[NH;D2;+0:4]-C=O):[#7;a:5]:[c:6]2:[#7;a:7](-[#8:8]):[c:9]:[#7;a:10]:[c:11]:2:1.[C;D1;H3:12]-[O-;H0;D1:13]>>[#8:8]-[#7;a:7]1:[c:9]:[#7;a:10]:[c:11]2:[c:6]:1:[#7;a:5]:[c:3](-[NH2;D1;+0:4]):[#7;a:2]:[c;H0;D3;+0:1]:2-[O;H0;D2;+0:13]-[C;D1;H3:12] | 76 | [{"value": 76.0, "product": "NC1=NC(=C2N=CN(C2=N1)OCC1=CC=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 9-benzyloxy-6-chloro-2-formamidopurine (440 mg, 1.60 mmol), 1.2M sodium methoxide in methanol (5.3 ml) and methanol (10 ml) was heated at reflux temperature for 1 hour and then cooled. Acetic acid (4 ml) was added and the solution evaporated to dryness. The residue was suspended in water and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Ether.Primary amine | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.c1ccccc1 | Other | CO | null | null | C[O-].O=CNc1nc(Cl)c2ncn(OCc3ccccc3)c2n1>CO>COc1nc(N)nc2c1ncn2OCc1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-cf9e57ba9a5d488b84ad34a0e5f55896 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.OC[C@@H](O)COCc1ccccc1>>CC(C)(C)[Si](OC[C@@H](O)COCc1ccccc1)(c1ccccc1)c1ccccc1 | N1C=NC=C1.[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)Cl.C(C1=CC=CC=C1)OC[C@@H](CO)O.C(C)(=O)O>>C(C1=CC=CC=C1)OC[C@@H](CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[OH:6][CH2:7][C@@H:8]([OH:9])[CH2:10][O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][C@@H:8]([OH:9])[CH2:10][O:11][CH2:12][c:13]1[... | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.OC[C@@H](O)COCc1ccccc1 | CC(C)(C)[Si](OC[C@@H](O)COCc1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C1CCOC1 | Protection | Alcohol protection with silyl ethers | 16b089e75ae0faeb6299d6901714a961ddf80ba40eb5191df04d4efe8b4a1af5 | a12fb6ee4294c877f426f603ce64d893e39b302f1553f4ca246c599e7a8e7068 | c1ccc(COCCCO[SiH](c2ccccc2)c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13]-[OH;D1;+0:14]>>[C:12]-[C:13]-[O;H0;D2;+0:14]-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)OC[C@@H](CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | MINUTE | To a solution of (R)-3-benzyloxypropane-1,2-diol (prepared from (S)-4-benzylymethyl-2,2-dimethyl-1,3-dioxolane (commercially available from FLUKA) by acid hydrolysis using 80% aqueous acetic acid), (8.3 g, 47.2 mmol) in dry THF (70 ml) was added imidazole (6.42 g, 94.4 mmol). After 2 minutes, t-butyldiphenylsilyl chlor... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Silyl protective group | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C1CCOC1 | null | 0.033333 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.OC[C@@H](O)COCc1ccccc1>C1CCOC1>CC(C)(C)[Si](OC[C@@H](O)COCc1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-f1025d795abd4352a2b488c82920f958 | CCOP(=O)(CO[C@@H](COCc1ccccc1)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>>CCOP(=O)(CO[C@@H](CO)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | C(C1=CC=CC=C1)OC[C@H](OCP(OCC)(OCC)=O)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C.[H][H].C(Cl)Cl.CO>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@H](CO)OCP(OCC)(OCC)=O | c1ccc(C[O:10][CH2:9][C@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:30][CH2:31][CH3:32])[CH2:11][O:12][Si:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[C:26]([CH3:27])([CH3:28])[CH3:29])cc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][C@@H:8]([CH2:9][OH:10])[CH... | CCOP(=O)(CO[C@@H](COCc1ccccc1)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | CCOP(=O)(CO[C@@H](CO)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | null | [Pd].CO.Cl | C(C)O | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ccc([SiH2]c2ccccc2)cc1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3] | 85.1 | [{"value": 84.0, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@H](CO)OCP(OCC)(OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@H](CO)OCP(OCC)(OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of diethyl (S)-[2-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)ethoxy]methylphosphonate (1.90 g, 3.3 mmol) in ethanol (20 ml) containing a trace of methanol/HCl (10 drops), was added 10%Pd-C (1.2 g). The mixture was shaken under an atmosphere of hydrogen at ambient temperature and atmospheric pressure until... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | [Pd].CO.Cl.C(C)O | null | null | CCOP(=O)(CO[C@@H](COCc1ccccc1)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>[Pd].CO.Cl.C(C)O>CCOP(=O)(CO[C@@H](CO)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d116ce1f21454e0fb2ec32831764af29 | CCOP(=O)(CO[C@@H](COCc1ccccc1)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>>CCOP(=O)(CO[C@H](CO)COCc1ccccc1)OCC | C(C1=CC=CC=C1)OC[C@H](OCP(OCC)(OCC)=O)CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C.N>>C(C1=CC=CC=C1)OC[C@H](OCP(OCC)(OCC)=O)CO | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:10][CH2:9][C@@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:20][CH2:21][CH3:22])[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][C@H:8]([CH2:9][OH:10])[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:1... | CCOP(=O)(CO[C@@H](COCc1ccccc1)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | CCOP(=O)(CO[C@H](CO)COCc1ccccc1)OCC | null | null | FC(C(=O)O)(F)F.O | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ccccc1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of diethyl (S)-[2-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)ethoxy]methylphosphonate (3.09 g, 5.4 mmol) in trifluoroacetic acid/water 2:1 (12 ml) was stirred at ambient temperature for 1 hour. The solution obtained was extracted with hexane (2×10 ml) and the aqueous containing phase evaporated to dryness.... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | c1ccccc1 | Other | FC(C(=O)O)(F)F.O | null | 1 | CCOP(=O)(CO[C@@H](COCc1ccccc1)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>FC(C(=O)O)(F)F.O>CCOP(=O)(CO[C@H](CO)COCc1ccccc1)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a5113e4fda5d4aa09565a60ed377bd33 | CCOP(=O)(COCCOn1cnc2c(Cl)ncnc21)OCC.N>>CCOP(=O)(COCCOn1cnc2c(N)ncnc21)OCC | ClC1=C2N=CN(C2=NC=N1)OCCOCP(=O)(OCC)OCC.N>>C(C)OP(=O)(OCC)COCCON1C2=NC=NC(=C2N=C1)N | Cl[c:15]1[c:14]2[n:13][cH:12][n:11]([O:10][CH2:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:21][CH2:22][CH3:23])[c:20]2[n:19][cH:18][n:17]1.[NH3:16]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][CH2:9][O:10][n:11]1[cH:12][n:13][c:14]2[c:15]([NH2:16])[n:17][cH:18][n:19][c:20]12)[O:21][CH2:22][CH3:23... | CCOP(=O)(COCCOn1cnc2c(Cl)ncnc21)OCC.N | CCOP(=O)(COCCOn1cnc2c(N)ncnc21)OCC | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d1ce4daf8ecb5816a05bfd6b5c1acf9fbd8b669f52cd7e645f544d6a4a7dba23 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ncc2nc[nH]c2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[#7;a:6](-[#8:7]):[c:8]:[#7;a:9]:[c:10]:2:1.[NH3;D0;+0:11]>>[#8:7]-[#7;a:6]1:[c:8]:[#7;a:9]:[c:10]2:[c:5]:1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | A solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]purine (1.45 g, 4 mmol) in ethanol (20 ml) saturated with ammonia gas was heated in a sealed steel vessel at 100° C. for 2 hours. The reaction mixture was cooled to ambient temperature, evaporated to dryness and the residual oil chromatographed on silica gel... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1ncnc2nc[nH]c12 | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | HCl | C(C)O | null | null | CCOP(=O)(COCCOn1cnc2c(Cl)ncnc21)OCC.N>C(C)O>CCOP(=O)(COCCOn1cnc2c(N)ncnc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5ee968f7cd244e5c82b70d125ecc7106 | CCOP(=O)(COCCOn1cnc2c(N)ncnc21)OCC>>Nc1ncnc2c1ncn2OCCOCP(=O)(O)O | C(C)OP(=O)(OCC)COCCON1C2=NC=NC(=C2N=C1)N.C[Si](C)(C)Br>>P(=O)(O)(O)COCCON1C2=NC=NC(=C2N=C1)N | CC[O:18][P:16]([CH2:15][O:14][CH2:13][CH2:12][O:11][n:10]1[c:6]2[n:5][cH:4][n:3][c:2]([NH2:1])[c:7]2[n:8][cH:9]1)(=[O:17])[O:19]CC>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[O:11][CH2:12][CH2:13][O:14][CH2:15][P:16](=[O:17])([OH:18])[OH:19] | CCOP(=O)(COCCOn1cnc2c(N)ncnc21)OCC | Nc1ncnc2c1ncn2OCCOCP(=O)(O)O | null | null | ClCCl | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ncc2nc[nH]c2n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | null | [] | null | null | 2 | HOUR | To a solution of 9-[2-(diethoxyphosphorylmethoxy)ethoxy]adenine (0.63 g, 1.83 mmol) in dry dichloromethane (10 ml) was added trimethylsilyl bromide (1.45 ml, 11 mmol) and the solution stirred at ambient temperature for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in methanol (10 ml)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2nc[nH]c12 | Other | ClCCl | null | 2 | CCOP(=O)(COCCOn1cnc2c(N)ncnc21)OCC>ClCCl>Nc1ncnc2c1ncn2OCCOCP(=O)(O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0650dbba12e64ab9a33df5f5a561be3d | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC.C[O-]>>COc1nc(N)nc2nc[nH]c12 | C(C)(=O)O.ClC1=C2N=CN(C2=NC(=N1)NC=O)OCCOCP(=O)(OCC)OCC.C[O-].[Na+]>>NC1=NC(=C2NC=NC2=N1)OC | CCOP(=O)(COCCO[n:11]1[cH:10][n:9][c:8]2[c:3](Cl)[n:4][c:5]([NH:6]C=O)[n:7][c:12]21)OCC.[CH3:1][O-:2]>>[CH3:1][O:2][c:3]1[n:4][c:5]([NH2:6])[n:7][c:8]2[n:9][cH:10][nH:11][c:12]12 | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC.C[O-] | COc1nc(N)nc2nc[nH]c12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 29302906f757069977d54f5256d18967805cdbf048e50538d5765a670dc77017 | 8b9073e4b8b44c62bad5709cc6af3ed157fdd23c44922de0fb49d759f30f9083 | c1ncc2[nH]cnc2n1 | C-C-O-P(=O)(-C-O-C-C-O-[n;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4]2:[c;H0;D3;+0:5]:1:[n;H0;D2;+0:6]:[c:7](-[NH;D2;+0:8]-C=O):[#7;a:9]:[c;H0;D3;+0:10]:2-Cl)-O-C-C.[C;D1;H3:11]-[O-;H0;D1:12]>>[C;D1;H3:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:10]1:[#7;a:9]:[c:7](-[NH2;D1;+0:8]):[n;H0;D2;+0:6]:[c;H0;D3;+0:4]2:[#7;a:3]:[c:2]:[nH;D... | null | [] | 50 | CELSIUS | null | null | To a solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.25 g, 0.61 mmol) in methanol (5 ml), was added sodium methoxide solution (30 wt % in methanol; 0.5 ml, 2.62 mmol). The mixture was stirred and heated at 50° C. for 4 hours. After cooling to ambient temperature, 80% aqueous acetic aci... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary amide | Ether.Primary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | CO | 50 | null | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC.C[O-]>CO>COc1nc(N)nc2nc[nH]c12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a41c8a765ab1473ab14b8ae1cb18f13d | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC.N>>CCOP(=O)(COCCOn1cnc2c(N)nc(N)nc21)OCC | ClC1=C2N=CN(C2=NC(=N1)NC=O)OCCOCP(=O)(OCC)OCC.N>>NC1=NC(=C2N=CN(C2=N1)OCCOCP(=O)(OCC)OCC)N | O=C[NH:19][c:18]1[n:17][c:15](Cl)[c:14]2[n:13][cH:12][n:11]([O:10][CH2:9][CH2:8][O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:22][CH2:23][CH3:24])[c:21]2[n:20]1.[NH3:16]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH2:8][CH2:9][O:10][n:11]1[cH:12][n:13][c:14]2[c:15]([NH2:16])[n:17][c:18]([NH2:19])[n:20][c:21]12)[... | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC.N | CCOP(=O)(COCCOn1cnc2c(N)nc(N)nc21)OCC | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | ec53b6621b81f23ad11820d7720ca4448dc242b7302068eb0da9fd1d5a9b9c87 | 0832ad55eec7798be0df2c65411db3d4ba73872698a651033a907cdb5603a4cf | c1ncc2nc[nH]c2n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[NH;D2;+0:4]-C=O):[#7;a:5]:[c:6]2:[#7;a:7](-[#8:8]):[c:9]:[#7;a:10]:[c:11]:2:1.[NH3;D0;+0:12]>>[#8:8]-[#7;a:7]1:[c:9]:[#7;a:10]:[c:11]2:[c:6]:1:[#7;a:5]:[c:3](-[NH2;D1;+0:4]):[#7;a:2]:[c;H0;D3;+0:1]:2-[NH2;D1;+0:12] | 35 | [{"value": 35.0, "product": "NC1=NC(=C2N=CN(C2=N1)OCCOCP(=O)(OCC)OCC)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.80 g, 1.96 mmol) in ethanol (10 ml) saturated with ammonia gas was heated in a sealed steel vessel at 110° C. for 51/2 hours. The reaction mixture was cooled to ambient temperature, evaporated to dryness and the residue chromatographed ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Primary amine.Primary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | C(C)O | null | null | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC.N>C(C)O>CCOP(=O)(COCCOn1cnc2c(N)nc(N)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-50227d33500b424e96daaaee51dff469 | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC>>Nc1nc(Cl)c2ncn(OCCOCP(=O)(O)O)c2n1 | ClC1=C2N=CN(C2=NC(=N1)NC=O)OCCOCP(=O)(OCC)OCC.C[Si](C)(C)Br>>NC1=NC(=C2N=CN(C2=N1)OCCOCP(=O)(O)O)Cl | CC[O:17][P:15]([CH2:14][O:13][CH2:12][CH2:11][O:10][n:9]1[cH:8][n:7][c:6]2[c:4]([Cl:5])[n:3][c:2]([NH:1]C=O)[n:20][c:19]21)(=[O:16])[O:18]CC>>[NH2:1][c:2]1[n:3][c:4]([Cl:5])[c:6]2[n:7][cH:8][n:9]([O:10][CH2:11][CH2:12][O:13][CH2:14][P:15](=[O:16])([OH:17])[OH:18])[c:19]2[n:20]1 | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC | Nc1nc(Cl)c2ncn(OCCOCP(=O)(O)O)c2n1 | null | null | CN(C=O)C | Reduction | OtherReaction | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ncc2nc[nH]c2n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C.O=C-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9](:[#7;a:10]):[c:11](:[#7;a:12]):[c:13]:[#7;a:14]:1>>[#7;a:12]:[c:11]1:[c:13]:[#7;a:14]:[c:7](-[NH2;D1;+0:6]):[#7;a:8]:[c:9]:1:[#7;a:10].[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | 51 | [{"value": 51.0, "product": "NC1=NC(=C2N=CN(C2=N1)OCCOCP(=O)(O)O)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.9, "product": "NC1=NC(=C2N=CN(C2=N1)OCCOCP(=O)(O)O)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.370 g, 0.91 mmol) in dry dimethylformamide (5 ml) was added trimethylsilyl bromide (1.3 ml, 9.6 mmol) and the solution stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the residue co-evap... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ncc2[nH]cnc2n1 | HO- | CN(C=O)C | null | 3 | CCOP(=O)(COCCOn1cnc2c(Cl)nc(NC=O)nc21)OCC>CN(C=O)C>Nc1nc(Cl)c2ncn(OCCOCP(=O)(O)O)c2n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-190b9092bb4642abb940ff079221ae89 | CCOP(=O)(COC(COC(C)=O)COn1cnc2c(Cl)nc(NC=O)nc21)OCC.N>>CCOP(=O)(COC(CO)COn1cnc2c(N)nc(N)nc21)OCC | C(C)(=O)OCC(CON1C2=NC(=NC(=C2N=C1)Cl)NC=O)OCP(=O)(OCC)OCC.N>>NC1=NC(=C2N=CN(C2=N1)OCC(CO)OCP(=O)(OCC)OCC)N | CC(=O)[O:10][CH2:9][CH:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:24][CH2:25][CH3:26])[CH2:11][O:12][n:13]1[cH:14][n:15][c:16]2[c:17](Cl)[n:19][c:20]([NH:21]C=O)[n:22][c:23]12.[NH3:18]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][CH:8]([CH2:9][OH:10])[CH2:11][O:12][n:13]1[cH:14][n:15][c:16]2[c:17]([NH2:18])[... | CCOP(=O)(COC(COC(C)=O)COn1cnc2c(Cl)nc(NC=O)nc21)OCC.N | CCOP(=O)(COC(CO)COn1cnc2c(N)nc(N)nc21)OCC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4ac034640febc53891e3a93473cd2bdc3be6df600c334943ccf72e5e4520dbf4 | cd484e6e59dd504cc717c49a9a8245d49da6b9a754eaab0dfcb4f23dd72e598e | c1ncc2nc[nH]c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3].Cl-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6](-[NH;D2;+0:7]-C=O):[#7;a:8]:[c:9]2:[#7;a:10](-[#8:11]):[c:12]:[#7;a:13]:[c:14]:2:1.[NH3;D0;+0:15]>>[#8:11]-[#7;a:10]1:[c:12]:[#7;a:13]:[c:14]2:[c:9]:1:[#7;a:8]:[c:6](-[NH2;D1;+0:7]):[#7;a:5]:[c;H0;D3;+0:4]:2-[NH2;D1;+0:15].[C:3]-[C:2]-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of 9-[3-acetoxy-2-(diethoxyphosphorylmethoxy)propoxy]-6-chloro-2-formamidopurine (0.16 g, 0.33 mmol) in ethanolic ammonia (5 ml) was heated in a sealed vessel at 120° C. for 5 hours. The solution was allowed to cool to ambient temperature and the solvent was removed under reduced pressure to leave a brown re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Secondary amide | Primary alcohol.Primary amine.Primary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCOP(=O)(COC(COC(C)=O)COn1cnc2c(Cl)nc(NC=O)nc21)OCC.N>>CCOP(=O)(COC(CO)COn1cnc2c(N)nc(N)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-fb64a9eb03c842dabe15b47f3ffd28fe | CCOP(=O)(CO[C@@H](CO)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC.COc1nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc2c1ncn2O>>CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@H](CO)OCP(OCC)(OCC)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)O)OC)C(=O)OC(C)(C)C.N(=NC(=O)OCC)C(=O)OCC>>C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@@H](CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C | O[CH2:9][C@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:56][CH2:57][CH3:58])[CH2:37][O:38][Si:39]([c:40]1[cH:41][cH:42][cH:43][cH:44][cH:45]1)([c:46]1[cH:47][cH:48][cH:49][cH:50][cH:51]1)[C:52]([CH3:53])([CH3:54])[CH3:55].[OH:10][n:11]1[cH:12][n:13][c:14]2[c:15]([O:16][CH3:17])[n:18][c:19]([N:20]([C:21](=[O:22... | CCOP(=O)(CO[C@@H](CO)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC.COc1nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc2c1ncn2O | CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0fcd381b777d6629b0c9e6356597dd7aaabef76c7dfe47721d8d10b5fc8adb37 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | c1ccc([SiH](OCCCOn2cnc3cncnc32)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[C:2](-[#8:3])-[C:4].[#7;a:5]:[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:1-[OH;D1;+0:11]>>[#7;a:5]:[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:1-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[#8:3])-[C:4] | 32.8 | [{"value": 32.0, "product": "C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@@H](CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@@H](CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)OC... | null | null | 1 | HOUR | To a stirred mixture of diethyl (S)-[1-(t-butyldiphenylsilyloxymethyl)-2-hydroxyethoxy]methylphosphonate (540 mg, 1.12 mmol), triphenylphosphine (440 mg, 1.68 mmol) and 2-[bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurine (prepared as described in EF-A-319228) (428 mg, 1.12 mmol) in dry THF (20 ml), cooled in ice ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | null | 1 | CCOP(=O)(CO[C@@H](CO)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC.COc1nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc2c1ncn2O>C1CCOC1>CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3adadfaf6a7e475a88305c15d84145c4 | CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>>CCOP(=O)(CO[C@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC | C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@@H](CO[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C>>NC1=NC(=C2N=CN(C2=N1)OC[C@@H](CO)OCP(=O)(OCC)OCC)OC | CC(C)(C)OC(=O)[N:22](C(=O)OC(C)(C)C)[c:21]1[n:20][c:17]([O:18][CH3:19])[c:16]2[n:15][cH:14][n:13]([O:12][CH2:11][C@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:25][CH2:26][CH3:27])[CH2:9][O:10][Si](c3ccccc3)(c3ccccc3)C(C)(C)C)[c:24]2[n:23]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][C@H:8]([CH2:9][OH:10])[... | CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | CCOP(=O)(CO[C@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 742a788aa080143cb95e67dbbc26ae175824fbb0417a64e4e60023f41494a9e1 | 831e261f8f25b25aded89607ca2fc6289d9df65bd75b82935fd6405170eea6b1 | c1ncc2nc[nH]c2n1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-C(=O)-O-C(-C)(-C)-C)-[c:2]1:[#7;a:3]:[c:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[#7;a:9]:1.C-C(-C)(-C)-[Si](-[O;H0;D2;+0:10]-[C:11]-[C:12])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[#7;a:8]:[c:7]1:[#7;a:9]:[c:2](-[NH2;D1;+0:1]):[#7;a:3]:[c:4]:[c:5]:1:[#7;a:6].[C:12]-[C:11]-[OH;D1;+0:10] | 70 | [{"value": 70.0, "product": "NC1=NC(=C2N=CN(C2=N1)OC[C@@H](CO)OCP(=O)(OCC)OCC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.2, "product": "NC1=NC(=C2N=CN(C2=N1)OC[C@@H](CO)OCP(=O)(OCC)OCC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (S)-2-[bis-(t-butyloxycarbonyl)amino]-9-[3-(t-butyldiphenylsilyloxy)-2-(diethoxyphosphorylmethoxy)propoxy]-6-methoxypurine (300 mg, 0.36 mmol) in 67% aqueous trifluoroacetic acid (3 ml) was kept at ambient temperature for 3 hours. The solution was washed with hexane (3×10 ml) and the aqueous phase evapora... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Substituted dicarboximide.Silyl protective group.Boc.Boc | Primary alcohol.Primary amine | c1ccccc1.c1ccccc1 | null | c1ncc2nc[nH]c2n1 | HO- | FC(C(=O)O)(F)F | null | null | CCOP(=O)(CO[C@@H](COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>FC(C(=O)O)(F)F>CCOP(=O)(CO[C@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-582e76d720ad40bb92003abde5f4f836 | CCOP(=O)(CO[C@@H](COn1cnc2c(N)ncnc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>>CCOP(=O)(CO[C@H](CO)COn1cnc2c(N)ncnc21)OCC | [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@H](CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(OCC)OCC.CCCCCC>>C(C)OP(=O)(OCC)CO[C@@H](CON1C2=NC=NC(=C2N=C1)N)CO | CC(C)(C)[Si](c1ccccc1)(c1ccccc1)[O:10][CH2:9][C@@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:23][CH2:24][CH3:25])[CH2:11][O:12][n:13]1[cH:14][n:15][c:16]2[c:17]([NH2:18])[n:19][cH:20][n:21][c:22]12>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][C@H:8]([CH2:9][OH:10])[CH2:11][O:12][n:13]1[cH:14][n:15][c:16]2[c... | CCOP(=O)(CO[C@@H](COn1cnc2c(N)ncnc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC | CCOP(=O)(CO[C@H](CO)COn1cnc2c(N)ncnc21)OCC | null | null | FC(C(=O)O)(F)F.O | Deprotection | Alcohol deprotection from silyl ethers | 5607047bc82bb27c5a65769b01ea0774767f4428c871f65da0b6352111d7a6e9 | 5c02ee98cb6b210a313993bea9e102110eb73637a50746f5457590f98613069b | c1ncc2nc[nH]c2n1 | C-C(-C)(-C)-[Si](-[O;H0;D2;+0:1]-[C:2]-[C:3])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[OH;D1;+0:1] | 80 | [{"value": 80.0, "product": "C(C)OP(=O)(OCC)CO[C@@H](CON1C2=NC=NC(=C2N=C1)N)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.9, "product": "C(C)OP(=O)(OCC)CO[C@@H](CON1C2=NC=NC(=C2N=C1)N)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | (S)-9-[3-(t-Butyldiphenylsilyloxy)-2-(diethoxyphosphorylmethoxy)propoxy]adenine (0.61 g, 1 mmol) was dissolved in trifluoroacetic acid/water, 2:1 (6 ml) and the solution stirred at ambient temperature for 3 hours. Hexane (10 ml) was added and the mixture shaken. The aqueous phase was separated, washed once more with he... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Primary alcohol | c1ccccc1.c1ccccc1 | null | c1ncnc2[nH]cnc12 | Other | FC(C(=O)O)(F)F.O | null | 3 | CCOP(=O)(CO[C@@H](COn1cnc2c(N)ncnc21)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OCC>FC(C(=O)O)(F)F.O>CCOP(=O)(CO[C@H](CO)COn1cnc2c(N)ncnc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b20bae2f00b74399b5f10481617ec119 | CCOP(=O)(CO[C@H](CO)COn1cnc2c(N)ncnc21)OCC>>Nc1ncnc2c1ncn2OC[C@@H](CO)OCP(=O)(O)O | C(C)OP(=O)(OCC)CO[C@@H](CON1C2=NC=NC(=C2N=C1)N)CO.C[Si](C)(C)Br>>OC[C@H](CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(O)O | CC[O:20][P:18]([CH2:17][O:16][C@@H:13]([CH2:12][O:11][n:10]1[c:6]2[n:5][cH:4][n:3][c:2]([NH2:1])[c:7]2[n:8][cH:9]1)[CH2:14][OH:15])(=[O:19])[O:21]CC>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[O:11][CH2:12][C@@H:13]([CH2:14][OH:15])[O:16][CH2:17][P:18](=[O:19])([OH:20])[OH:21] | CCOP(=O)(CO[C@H](CO)COn1cnc2c(N)ncnc21)OCC | Nc1ncnc2c1ncn2OC[C@@H](CO)OCP(=O)(O)O | null | null | CN(C)C=O | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ncc2nc[nH]c2n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | null | [] | null | null | 4 | HOUR | To a solution of (R)-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy)adenine (0.16 g, 0.43 mmol) in dry DMF (3 ml) was added trimethylsilyl bromide (0.56 ml, 4.3 mmol) and the solution stirred at ambient temperature for 4 hours. The solvent was removed under reduced presence and the residue co-evaporated with acetone... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2nc[nH]c12 | Other | CN(C)C=O | null | 4 | CCOP(=O)(CO[C@H](CO)COn1cnc2c(N)ncnc21)OCC>CN(C)C=O>Nc1ncnc2c1ncn2OC[C@@H](CO)OCP(=O)(O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-5bc3817b8fb84fdcb2e908b50be90647 | CCOP(=O)(CO[C@H](CO)COCc1ccccc1)OCC.COc1nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc2c1ncn2O>>CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)OCC | N(=NC(=O)OCC)C(=O)OCC.C(C1=CC=CC=C1)OC[C@H](OCP(OCC)(OCC)=O)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)O)OC)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@H](COCC1=CC=CC=C1)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C | O[CH2:18][C@@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:46][CH2:47][CH3:48])[CH2:9][O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[OH:19][n:20]1[cH:21][n:22][c:23]2[c:24]([O:25][CH3:26])[n:27][c:28]([N:29]([C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[C:37](=[O:38])[O:39][C:40]([CH3:41]... | CCOP(=O)(CO[C@H](CO)COCc1ccccc1)OCC.COc1nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc2c1ncn2O | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)OCC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 0fcd381b777d6629b0c9e6356597dd7aaabef76c7dfe47721d8d10b5fc8adb37 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | c1ccc(COCCCOn2cnc3cncnc32)cc1 | O-[CH2;D2;+0:1]-[C:2](-[#8:3])-[C:4].[#7;a:5]:[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:1-[OH;D1;+0:11]>>[#7;a:5]:[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:1-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[#8:3])-[C:4] | 88.6 | [{"value": 88.0, "product": "C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@H](COCC1=CC=CC=C1)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@H](COCC1=CC=CC=C1)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C", "details": "CALCULAT... | null | null | 16 | HOUR | To a stirred solution of diethyl (R)-[2-benzyloxy-1-(hydroxymethyl)ethoxy]methylphosphonate (1.0 g, 3 mmol), triphenylphosphine (1.18 g, 4.5 mmol) and 2-[bis-(t-butoxycarbonyl)amino]-9-hydroxy-6-methoxypurine (1.15 g, 3 mmol) in dry THF (20 ml), cooled in ice and under a mitrogen atmosphere, was added, dropwise, diethy... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | C1CCOC1 | null | 16 | CCOP(=O)(CO[C@H](CO)COCc1ccccc1)OCC.COc1nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc2c1ncn2O>C1CCOC1>CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4ec7e441b65e463e8f7ca2919ba87390 | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)OCC>>CCOP(=O)(CO[C@@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC | ClCCl.CO.ClCCl.CO.FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)N(C1=NC(=C2N=CN(C2=N1)OC[C@H](COCC1=CC=CC=C1)OCP(=O)(OCC)OCC)OC)C(=O)OC(C)(C)C>>NC1=NC(=C2N=CN(C2=N1)OC[C@H](CO)OCP(=O)(OCC)OCC)OC | CC(C)(C)OC(=O)[N:22](C(=O)OC(C)(C)C)[c:21]1[n:20][c:17]([O:18][CH3:19])[c:16]2[n:15][cH:14][n:13]([O:12][CH2:11][C@@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:25][CH2:26][CH3:27])[CH2:9][O:10]Cc3ccccc3)[c:24]2[n:23]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][C@@H:8]([CH2:9][OH:10])[CH2:11][O:12][n:13]1[... | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)OCC | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC | null | [Pd] | ClCCl | Reduction | OtherReaction | 846198111ba4e1b2f48d3946b032ec585935cd69d7cf5a22f26153063c459e73 | 782db24ab00d91ad9b44c8a3b748f0ddc56ae11ac546fc3fa2ca82912753169f | c1ncc2nc[nH]c2n1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-C(=O)-O-C(-C)(-C)-C)-[c:2]1:[#7;a:3]:[c:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[#7;a:9]:1.[C:10]-[C:11]-[O;H0;D2;+0:12]-C-c1:c:c:c:c:c:1>>[#7;a:8]:[c:7]1:[#7;a:9]:[c:2](-[NH2;D1;+0:1]):[#7;a:3]:[c:4]:[c:5]:1:[#7;a:6].[C:10]-[C:11]-[OH;D1;+0:12] | 69.7 | [{"value": 67.0, "product": "NC1=NC(=C2N=CN(C2=N1)OC[C@H](CO)OCP(=O)(OCC)OCC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "NC1=NC(=C2N=CN(C2=N1)OC[C@H](CO)OCP(=O)(OCC)OCC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Trifluoroacetic acid (2 ml) was added to an ice cooled solution of (S)-2-[bis-(t-butoxycarbonyl)amino]-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy]propoxy]-6-methoxypurine (1.65 g, 2.3 mmol) in dry dichloromethane (30 ml) an the resulting solution left for 2 hours. After warming to ambient temperature, 10% Pd-C (800 mg... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Ether.Substituted dicarboximide.Boc.Boc | Primary alcohol.Primary amine | c1ccccc1 | null | c1ncc2nc[nH]c2n1 | HO- | [Pd].ClCCl | null | 2 | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(OC)nc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)nc21)OCC>[Pd].ClCCl>CCOP(=O)(CO[C@@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-45efcb5ccf7b442ba9f977b45016c6dc | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC>>Nc1nc2c(ncn2OC[C@H](CO)OCP(=O)(O)O)c(=O)[nH]1 | NC1=NC(=C2N=CN(C2=N1)OC[C@H](CO)OCP(=O)(OCC)OCC)OC.C[Si](C)(C)Br>>OC[C@@H](CON1C=2N=C(NC(C2N=C1)=O)N)OCP(=O)(O)O | CC[O:18][P:16]([CH2:15][O:14][C@H:11]([CH2:10][O:9][n:8]1[c:4]2[n:3][c:2]([NH2:1])[n:22][c:20]([O:21]C)[c:5]2[n:6][cH:7]1)[CH2:12][OH:13])(=[O:17])[O:19]CC>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[O:9][CH2:10][C@H:11]([CH2:12][OH:13])[O:14][CH2:15][P:16](=[O:17])([OH:18])[OH:19])[c:20](=[O:21])[nH:22]1 | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC | Nc1nc2c(ncn2OC[C@H](CO)OCP(=O)(O)O)c(=O)[nH]1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 7df42013a8a82d16a16a8ebd2642f2da22626e53d9da131c05420004be26e355 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1[nH]cnc2[nH]cnc12 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C.C-[O;H0;D2;+0:6]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:8]:[c:9](-[N;D1;H2:10]):[#7;a:11]:[c:12]2:[#7;a:13](-[#8:14]):[c:15]:[#7;a:16]:[c:17]:2:1>>[#8:14]-[#7;a:13]1:[c:15]:[#7;a:16]:[c:17]2:[c:12]:1:[#7;a:11]:[c:9](-[N;D1;H2:10]):[nH;D2;+0:8]:[c;H0;D3;+0:7]:2=[O... | 66 | [{"value": 66.0, "product": "OC[C@@H](CON1C=2N=C(NC(C2N=C1)=O)N)OCP(=O)(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "OC[C@@H](CON1C=2N=C(NC(C2N=C1)=O)N)OCP(=O)(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of (S)-2-amino-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]-6-methoxypurine (0.56 g, 1.38 mmol) in dry dimethylformamide (5 ml) was added trimethylsilyl bromide (1.82 ml, 13.8 mmol) and the solution stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the re... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | CN(C=O)C | null | 3 | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(OC)nc(N)nc21)OCC>CN(C=O)C>Nc1nc2c(ncn2OC[C@H](CO)OCP(=O)(O)O)c(=O)[nH]1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0d06f94fdd1c4633bb83d7bfd253bf39 | Nc1nc2c(ncn2OC[C@H](CO)OCP(=O)(O)O)c(=O)[nH]1>>Nc1nc2c(ncn2OC[C@@H]2COP(=O)(O)CO2)c(=O)[nH]1 | C1(CCCCC1)N=C=NC1CCCCC1.OC[C@@H](CON1C=2N=C(NC(C2N=C1)=O)N)OCP(=O)(O)O>>OP1(OC[C@H](OC1)CON1C=2N=C(NC(C2N=C1)=O)N)=O | O[P:14](=[O:15])([OH:16])[CH2:17][O:18][C@H:11]([CH2:10][O:9][n:8]1[c:4]2[n:3][c:2]([NH2:1])[nH:21][c:19](=[O:20])[c:5]2[n:6][cH:7]1)[CH2:12][OH:13]>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[O:9][CH2:10][C@@H:11]2[CH2:12][O:13][P:14](=[O:15])([OH:16])[CH2:17][O:18]2)[c:19](=[O:20])[nH:21]1 | Nc1nc2c(ncn2OC[C@H](CO)OCP(=O)(O)O)c(=O)[nH]1 | Nc1nc2c(ncn2OC[C@@H]2COP(=O)(O)CO2)c(=O)[nH]1 | null | null | C(C)(C)(C)O | Miscellaneous | OtherReaction | e726f12fd2fdda4fd57362331cd94e1e476a8a8295b64014296d8797e7159eb8 | 0450d2d3d6169ebd913d75de6102597ba0029b73d4e4cd2ca50ccc23bda73392 | O=c1[nH]cnc2c1ncn2OC[C@@H]1CO[PH](=O)CO1 | O-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;D1;H1:3])-[C:4]-[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[O;D1;H0:2]=[P;H0;D4;+0:1]1(-[O;D1;H1:3])-[C:4]-[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-1 | 59 | [{"value": 59.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of dicyclohexylcarbodiimide (0.615 g, 3.0 mmol) in t-butanol (10 ml) was added dropwise over 30 minutes to a solution of (S)-9-[3-hydroxy-2-(phosphonomethoxy)propoxy]guanine (0.20 g, 0.6 mmol) and N,N-dicyclohexyl-4-morpholinocarboxamidine (0.175 g, 0.6 mmol) in 50% aqueous t-butanol (30 ml). The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | C1CO[P]CO1 | c1ncc2[nH]cnc2n1.C1CO[P]CO1 | HO- | C(C)(C)(C)O | null | null | Nc1nc2c(ncn2OC[C@H](CO)OCP(=O)(O)O)c(=O)[nH]1>C(C)(C)(C)O>Nc1nc2c(ncn2OC[C@@H]2COP(=O)(O)CO2)c(=O)[nH]1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-80bdae9dfd7846309df6346a394b17b5 | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(N)ncnc21)OCC>>CCOP(=O)(CO[C@@H](CO)COn1cnc2c(N)ncnc21)OCC | C(C1=CC=CC=C1)OC[C@@H](CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(OCC)OCC>>C(C)OP(=O)(OCC)CO[C@H](CON1C2=NC=NC(=C2N=C1)N)CO | c1ccc(C[O:10][CH2:9][C@H:8]([O:7][CH2:6][P:4]([O:3][CH2:2][CH3:1])(=[O:5])[O:23][CH2:24][CH3:25])[CH2:11][O:12][n:13]2[cH:14][n:15][c:16]3[c:17]([NH2:18])[n:19][cH:20][n:21][c:22]23)cc1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][O:7][C@@H:8]([CH2:9][OH:10])[CH2:11][O:12][n:13]1[cH:14][n:15][c:16]2[c:17]([NH2:18])[n:19][... | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(N)ncnc21)OCC | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(N)ncnc21)OCC | null | [Pd] | ClCCl.N.FC(C(=O)O)(F)F | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ncc2nc[nH]c2n1 | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3] | 65 | [{"value": 65.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 10% Pd-C (50 mg) was added to a solution of (S)-9-[3-benzyloxy-2-(diethoxyphosphorylmethoxy)propoxy]adenine (0.21 g, 0.45 mmol) in dichloromethane (5 ml) and trifluoroacetic acid (lml) and the mixture hydrogenated at atmospheric pressure and ambient temperature for 5 hours. The mixture was filtered, the filtrate evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1ncnc2[nH]cnc12 | Other | [Pd].ClCCl.N.FC(C(=O)O)(F)F | null | 5 | CCOP(=O)(CO[C@@H](COCc1ccccc1)COn1cnc2c(N)ncnc21)OCC>[Pd].ClCCl.N.FC(C(=O)O)(F)F>CCOP(=O)(CO[C@@H](CO)COn1cnc2c(N)ncnc21)OCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-1700e5b3912a4121a6882d243c1ca8a2 | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(N)ncnc21)OCC>>Nc1ncnc2c1ncn2OC[C@H](CO)OCP(=O)(O)O | C(C)OP(=O)(OCC)CO[C@H](CON1C2=NC=NC(=C2N=C1)N)CO.C[Si](C)(C)Br>>OC[C@@H](CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(O)O | CC[O:20][P:18]([CH2:17][O:16][C@H:13]([CH2:12][O:11][n:10]1[c:6]2[n:5][cH:4][n:3][c:2]([NH2:1])[c:7]2[n:8][cH:9]1)[CH2:14][OH:15])(=[O:19])[O:21]CC>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[O:11][CH2:12][C@H:13]([CH2:14][OH:15])[O:16][CH2:17][P:18](=[O:19])([OH:20])[OH:21] | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(N)ncnc21)OCC | Nc1ncnc2c1ncn2OC[C@H](CO)OCP(=O)(O)O | null | null | ClCCl | Deprotection | OtherReaction | eaaf8436ac19e7e26db9ff78e61eed5caf13b9167196c3230a9e1eb66b295f8b | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | c1ncc2nc[nH]c2n1 | C-C-[O;H0;D2;+0:1]-[#15:2](-[C:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-C>>[C:3]-[#15:2](=[O;D1;H0:4])(-[OH;D1;+0:1])-[OH;D1;+0:5] | 78.3 | [{"value": 78.0, "product": "OC[C@@H](CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "OC[C@@H](CON1C2=NC=NC(=C2N=C1)N)OCP(=O)(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of (S)-9-[2-(diethoxyphosphorylmethoxy)-3-hydroxypropoxy]adenine (0.09 g, 0.24 mmol) in dry dichloromethane (3 ml) was added trimethylsilyl bromide (0.31 ml, 2.4 mmol) and the solution stirred at ambient temperature for 4 hours. The solvent was removed under reduced pressure and the residue co-evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncnc2nc[nH]c12 | Other | ClCCl | null | 4 | CCOP(=O)(CO[C@@H](CO)COn1cnc2c(N)ncnc21)OCC>ClCCl>Nc1ncnc2c1ncn2OC[C@H](CO)OCP(=O)(O)O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d955b6bed1764bfcacbd148dda54d25f | C=CC(=O)[O-].CO[Si](CCCCl)(OC)OC>>C=CC(=O)OCCC[Si](OC)(OC)OC | ClCCC[Si](OC)(OC)OC.C(C=C)(=O)[O-].[K+]>>C(C=C)(=O)OCCC[Si](OC)(OC)OC | [CH2:1]=[CH:2][C:3](=[O:4])[O-:5].Cl[CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15]>>[CH2:1]=[CH:2][C:3](=[O:4])[O:5][CH2:6][CH2:7][CH2:8][Si:9]([O:10][CH3:11])([O:12][CH3:13])[O:14][CH3:15] | C=CC(=O)[O-].CO[Si](CCCCl)(OC)OC | C=CC(=O)OCCC[Si](OC)(OC)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | null | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H2:4]=[C:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:7]-[C:6](=[O;D1;H0:8])-[C:5]=[C;D1;H2:4] | null | [] | null | null | null | null | Trichlorosilane and allyl chloride were subjected to hydrosilylation reaction in a solvent in the presence of a platinum catalyst, followed by esterification reaction with methanol and urea and further by distillation to obtain γ-chloropropyltrimethoxysilane. The thus obtained γ-chloropropyltrimethoxysilane and potassi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | null | Other | null | null | null | C=CC(=O)[O-].CO[Si](CCCCl)(OC)OC>>C=CC(=O)OCCC[Si](OC)(OC)OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-994fe399445642c1ae38540975c70fa4 | C=CC#N.C=CC#N.N.N>>C=CC#N.N#CCCN.N#CCCNCCC#N | C(C=C)#N.N.N.N.C(C=C)#N>>N.C(C=C)#N.NCCC#N.C(#N)CCNCCC#N | [N:11]#[C:12][CH:13]=[CH2:14].[CH2:1]=[CH:17][C:3]#[N:4].[NH3:10].[NH3:15]>>[CH2:1]=[CH:2][C:3]#[N:4].[N:6]#[C:7][CH2:8][CH2:9][NH2:10].[N:11]#[C:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C:18]#[N:19] | C=CC#N.C=CC#N.N.N | C=CC#N.N#CCCN.N#CCCNCCC#N | null | null | O | Functional Group Addition | OtherReaction | d4bda893c7dbc2a572b03c20d8a406421e563a7ac48b91ed59978564dbf291fa | cb2527c2932ef3736f2cf1a1babe54e5439f77def1e19c1f6e429d549d43fe6c | null | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C;H0;D2;+0:3]#[N;D1;H0:4].[CH2;D1;+0:5]=[CH;D2;+0:6]-[C:7]#[N;D1;H0:8].[NH3;D0;+0:9].[NH3;D0;+0:10]>>[CH2;D1;+0:1]=[C:11]-[C;H0;D2;+0:3]#[N;D1;H0:4].[C:12]-[C:13]-[NH2;D1;+0:9].[N;D1;H0:8]#[C:7]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[NH;D2;+0:10]-[C:14]-[CH2;D2;+0:2]-[C:15]#[N;D1;H0:16] | null | [] | null | null | null | null | It is also known that the addition of protic solvents has an advantageous effect on the addition reaction of NH3 with acrylonitrile. The addition of steam to the mixture of acrylonitrile and ammonia is disclosed in, for example, Chem. Abstr. Vol. 83, 26879. Usually, however, aqueous ammonia is used in the temperature r... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Vinyl.Vinyl | Nitrile.Nitrile.Nitrile.Primary amine.Secondary amine.Vinyl | null | null | null | Other | O | null | null | C=CC#N.C=CC#N.N.N>O>C=CC#N.N#CCCN.N#CCCNCCC#N |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a8539b47ced44f24996e5458c2287ac2 | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O>>O=c1c(-c2ccccc2)coc2cc(O)ccc12 | OC1=C(C=CC(=C1)O)C(C1=CC=CC=C1)C(=O)C(C1=CC=CC=C1)C1=C(C=C(C=C1)O)O.N1CCOCC1.C(C)OC([O-])[O-]>>OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O | Oc1ccc(C(c2ccccc2)[C:2](=[O:1])[CH:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:18]2[c:12]([OH:11])[cH:13][c:14]([OH:15])[cH:16][cH:17]2)c(O)c1>>[O:1]=[c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[cH:10][o:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]12 | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O | O=c1c(-c2ccccc2)coc2cc(O)ccc12 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 5c46f3987737fa0f22228dd44a6bd6b7bd43b521e731bd2a0cfc314cc3527683 | 1bfc4d5805724ff11fd4e30627af394f8cac65c20e402464557ba08d5a7e84c6 | O=c1c(-c2ccccc2)coc2ccccc12 | O-c1:c:c:c(-C(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-c2:c:c:c:c:c:2):c(-O):c:1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:[c:15]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:10](:[c:1... | 91.9 | [{"value": 91.9, "product": "OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 50 g (0.219 mole) of a mixture of 2,4-dihydroxy-phenyl-benzyl-ketone, 20 ml of dimethyl-formamide, 2.6 ml of morpholine and 39.06 g (0.26 mole) of ethyl-orthoformate is stirred for 7 hours at 80°-90° C. After 25 minutes crystallization can be observed. At the end of the reaction time the crystallized suspension is dilu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1cc2ccccc2oc1 | c1ccccc1.c1cc2ccccc2oc1 | HO- | CN(C=O)C | null | null | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O>CN(C=O)C>O=c1c(-c2ccccc2)coc2cc(O)ccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-90f5082eeee942519d56cfae78d6b65a | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O>>O=c1c(-c2ccccc2)coc2cc(O)ccc12 | OC1=C(C=CC(=C1)O)C(C1=CC=CC=C1)C(=O)C(C1=CC=CC=C1)C1=C(C=C(C=C1)O)O.C(C)OC([O-])[O-].N1CCOCC1>>OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O | Oc1ccc(C(c2ccccc2)[C:2](=[O:1])[CH:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:18]2[c:12]([OH:11])[cH:13][c:14]([OH:15])[cH:16][cH:17]2)c(O)c1>>[O:1]=[c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[cH:10][o:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]12 | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O | O=c1c(-c2ccccc2)coc2cc(O)ccc12 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5c46f3987737fa0f22228dd44a6bd6b7bd43b521e731bd2a0cfc314cc3527683 | 1bfc4d5805724ff11fd4e30627af394f8cac65c20e402464557ba08d5a7e84c6 | O=c1c(-c2ccccc2)coc2ccccc12 | O-c1:c:c:c(-C(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-c2:c:c:c:c:c:2):c(-O):c:1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:[c:15]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:10](:[c:1... | 90.6 | [{"value": 90.6, "product": "OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 20 g (0.0877 mole) 2,4-dihydroxy-phenyl-benzyl-ketone, 20.7 g (0.14 mole) ethyl-orthoformate and 1 ml of morpholine is stirred on a hot water bath. Crystallization starts after heating for 25 minutes. The inert temperature falls back to 87° C. from 96° C. during the reaction. After stirring for 5 hours the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1cc2ccccc2oc1 | c1ccccc1.c1cc2ccccc2oc1 | HO- | C(Cl)(Cl)Cl | null | null | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O>C(Cl)(Cl)Cl>O=c1c(-c2ccccc2)coc2cc(O)ccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-e89dd36c6e3b43d29e69f02bfcdffabb | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O>>O=c1c(-c2ccccc2)coc2cc(O)ccc12 | OC1=C(C=CC(=C1)O)C(C1=CC=CC=C1)C(=O)C(C1=CC=CC=C1)C1=C(C=C(C=C1)O)O.CN(C=O)C.N1CCOCC1.C(C)OC([O-])[O-]>>OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O | Oc1ccc(C(c2ccccc2)[C:2](=[O:1])[CH:3]([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:18]2[c:12]([OH:11])[cH:13][c:14]([OH:15])[cH:16][cH:17]2)c(O)c1>>[O:1]=[c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[cH:10][o:11][c:12]2[cH:13][c:14]([OH:15])[cH:16][cH:17][c:18]12 | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O | O=c1c(-c2ccccc2)coc2cc(O)ccc12 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 5c46f3987737fa0f22228dd44a6bd6b7bd43b521e731bd2a0cfc314cc3527683 | 1bfc4d5805724ff11fd4e30627af394f8cac65c20e402464557ba08d5a7e84c6 | O=c1c(-c2ccccc2)coc2ccccc12 | O-c1:c:c:c(-C(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-c2:c:c:c:c:c:2):c(-O):c:1>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:[c:15]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:10](:[c:1... | 90.5 | [{"value": 90.5, "product": "OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "OC1=CC=C2C(C(=COC2=C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 100 kg (438.5 mole) of 2,4-dihydroxy-phenyl-benzyl-ketone, 38 kg of dimethyl-formamide, 5.2 kg of morpholine and 75 kg (506 mole) of ethyl-orthoformate is stirred at 80°-90° C., while within one hour crystallization is initiated. 360 kg of chloroform are added to the suspension after 7 hours at 60° C. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1cc2ccccc2oc1 | c1ccccc1.c1cc2ccccc2oc1 | HO- | C(Cl)(Cl)Cl | null | 1 | O=C(C(c1ccccc1)c1ccc(O)cc1O)C(c1ccccc1)c1ccc(O)cc1O>C(Cl)(Cl)Cl>O=c1c(-c2ccccc2)coc2cc(O)ccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d16c7c6433784192b16c37dc97ffc08b | COc1ccc(C(C(=O)C(c2ccc(OC)c(OC)c2)c2ccc(O)cc2O)c2ccc(O)cc2O)cc1OC>>COc1ccc(-c2coc3cc(O)ccc3c2=O)cc1OC | OC1=C(C=CC(=C1)O)C(C1=CC(=C(C=C1)OC)OC)C(=O)C(C1=CC(=C(C=C1)OC)OC)C1=C(C=C(C=C1)O)O.C(C)OC([O-])[O-].N1CCOCC1>>OC1=CC=C2C(C(=COC2=C1)C1=CC(=C(C=C1)OC)OC)=O | COc1ccc(C(c2ccc(O)cc2O)[C:17]([CH:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:20]([O:21][CH3:22])[cH:19]2)[c:16]2[c:10]([OH:9])[cH:11][c:12]([OH:13])[cH:14][cH:15]2)=[O:18])cc1OC>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][o:9][c:10]3[cH:11][c:12]([OH:13])[cH:14][cH:15][c:16]3[c:17]2=[O:18])[cH:19][c:20]1[O:21][C... | COc1ccc(C(C(=O)C(c2ccc(OC)c(OC)c2)c2ccc(O)cc2O)c2ccc(O)cc2O)cc1OC | COc1ccc(-c2coc3cc(O)ccc3c2=O)cc1OC | null | null | CN(C=O)C | Miscellaneous | OtherReaction | c7a7a463f7d1012652715db648ed8a1e0f63a65bcacb67bbe64ee0c02b3f2880 | accbf2130ca52c4bbc23fa759e1031930d201f7e2492c7bcd417d7bf428febee | O=c1c(-c2ccccc2)coc2ccccc12 | C-O-c1:c:c:c(-C(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](-[OH;D1;+0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-c2:c:c:c(-O):c:c:2-O):c:c:1-O-C>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7](:[c:9]):[o;H0;D2;+0:8]:[c:15]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:1... | null | [] | null | null | null | null | 14.4 g (0.05 mole) of 2,4-dihydroxy-phenyl-(3',4'-dimethoxy-benzyl)-ketone are reacted with 10.5 g (0.07 mole) ethyl-orthoformate in 10 ml of dimethyl-formamide in the presence of 1 ml morpholine. The reaction mixture is maintained at 80°-85° C., and in the second hour a solid precipitates. After 6 hours 1OO ml of chlo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol | null | c1ccccc1.c1ccccc1.c1ccccc1 | c1cc2ccccc2oc1 | c1ccccc1.c1cc2ccccc2oc1 | HO- | CN(C=O)C | null | null | COc1ccc(C(C(=O)C(c2ccc(OC)c(OC)c2)c2ccc(O)cc2O)c2ccc(O)cc2O)cc1OC>CN(C=O)C>COc1ccc(-c2coc3cc(O)ccc3c2=O)cc1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6c29b27eab4d4e1eb2642d9e68152ba2 | CC(=O)OCCc1ccc(OC(C)=O)cc1>>C=Cc1ccc(OC(C)=O)cc1 | O.C(C)(=O)OCCC1=CC=C(C=C1)OC(C)=O.C(C)(=O)OC(C)=O.P(O)(O)(O)=O.P(O)(O)(O)=O>>C(C)(=O)OC1=CC=C(C=C)C=C1 | CC(=O)O[CH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][C:8]([CH3:9])=[O:10])[cH:11][cH:12]1>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][C:8]([CH3:9])=[O:10])[cH:11][cH:12]1 | CC(=O)OCCc1ccc(OC(C)=O)cc1 | C=Cc1ccc(OC(C)=O)cc1 | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | 1e8369fb83bfa75d3610947e02abdc2c7888d69bd2ca051eae81d59d3fc6a793 | 024826f40b3dd6c221315523e73e00ea8d8ac8916ccd21c38235caffd155b82d | c1ccccc1 | C-C(=O)-O-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A flask heated by hot oil was fitted with a chilled water overhead condenser, a thermowell with a thermocouple, an overhead stirrer and a vacuum pump. Crude APMC-Ether (20 grams) containing 78.2 weight percent APMC-Ether, 7.2 weight percent APMC and 3.9 weight percent 4-acetoxyphenylmethylcarbinol acetate (sometimes re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Vinyl | null | null | c1ccccc1 | HO- | C(C)(=O)O | null | null | CC(=O)OCCc1ccc(OC(C)=O)cc1>C(C)(=O)O>C=Cc1ccc(OC(C)=O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3b52f1fff38f4058ba6f446cfd607f7d | COC(=O)C(Cl)CC(C)C1=CCC2C(OC(C)=O)CCCC12C>>CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CO)=CCC12 | [H-].[Al+3].[Li+].[H-].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(C(CC(C1=CCC2C(CCCC12C)OC(C)=O)C)Cl)=O>>C(C)(=O)OC1CCCC2(C(=CCC12)C(CC(CO)Cl)C)C | CO[C:17]([CH:15]([CH2:14][CH:12]([C:11]1=[CH:19][CH2:20][CH:21]2[CH:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:6][CH2:7][CH2:8][C:9]12[CH3:10])[CH3:13])[Cl:16])=[O:18]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][CH2:8][C:9]2([CH3:10])[C:11]([CH:12]([CH3:13])[CH2:14][CH:15]([Cl:16])[CH2:17][OH:18])=[CH:19][CH2:20][CH:21]12 | COC(=O)C(Cl)CC(C)C1=CCC2C(OC(C)=O)CCCC12C | CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CO)=CCC12 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1=CC2CCCCC2C1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[Cl;D1;H0:5]>>[C:4]-[C:3](-[Cl;D1;H0:5])-[CH2;D2;+0:1]-[OH;D1;+0:2] | 93 | [{"value": 93.0, "product": "C(C)(=O)OC1CCCC2(C(=CCC12)C(CC(CO)Cl)C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A solution of 1.01 g (2.95 mmol) of [3aS-[3(αS*, γR*),3aα,7β,7aβ]-7-(acetyloxy)-α-chloro-3a,4,5,6,7, 7a-hexahydro-γ,3a-dimethyl-1H-indene-3-butanoic acid methyl ester in 25 mL of anhydrous tetrahydrofuran was cooled at 0° C. and treated under argon with 1.47 mL (1.47 mmol) of a 1M solution of lithium aluminum hydride i... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=CC2CCCCC2C1 | Other | O1CCCC1 | 0 | 2 | COC(=O)C(Cl)CC(C)C1=CCC2C(OC(C)=O)CCCC12C>O1CCCC1>CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CO)=CCC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-df8f3ff397084a7f9ec3233d739fea5e | CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CO)=CCC12.[Br-]>>CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CBr)=CCC12 | [Br-].[Li+].O.C(C)(=O)OC1CCCC2(C(=CCC12)C(CC(CO)Cl)C)C.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C(C)(=O)OC1CCCC2(C(=CCC12)C(CC(CBr)Cl)C)C | O[CH2:17][CH:15]([CH2:14][CH:12]([C:11]1=[CH:19][CH2:20][CH:21]2[CH:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:6][CH2:7][CH2:8][C:9]12[CH3:10])[CH3:13])[Cl:16].[Br-:18]>>[CH3:1][C:2](=[O:3])[O:4][CH:5]1[CH2:6][CH2:7][CH2:8][C:9]2([CH3:10])[C:11]([CH:12]([CH3:13])[CH2:14][CH:15]([Cl:16])[CH2:17][Br:18])=[CH:19][CH2:20][CH:21]12 | CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CO)=CCC12.[Br-] | CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CBr)=CCC12 | null | null | ClCCl.N1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | C1=CC2CCCCC2C1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[Cl;D1;H0:4].[Br-;H0;D0:5]>>[Br;H0;D1;+0:5]-[CH2;D2;+0:1]-[C:2](-[C:3])-[Cl;D1;H0:4] | null | [] | 0 | CELSIUS | 8 | HOUR | A solution of 1.50 g (4.76 mmol) of [3aS-[3(βS*,δR*), 3aα,7β,7aβ]]-7-(acetyloxy)-β-chloro-3a,4,5,6,7,7a-hexahydro-δ,3a-dimethyl-1H-indene-3-butanol in 20 mL of dichloromethane and 20 mL of pyridine was treated at 0° C. and under argon with 4.50 g (23.60 mmol) of p-toluenesulfonyl chloride and then stirred overnight at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | C1=CC2CCCCC2C1 | HO- | ClCCl.N1=CC=CC=C1 | 0 | 8 | CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CO)=CCC12.[Br-]>ClCCl.N1=CC=CC=C1>CC(=O)OC1CCCC2(C)C(C(C)CC(Cl)CBr)=CCC12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4b6f82fdc15f49e3b6f995f7f804f355 | C1CCOC1.CC(C)[N-]C(C)C.[Li+]>>CC(C)NC(C)C.[Li][CH2]CCC | O1CCCC1.C(C)(C)[N-]C(C)C.[Li+]>>C(CCC)[Li].C(C)(C)NC(C)C | O1[CH2:10][CH2:9][CH2:12][CH2:11]1.[CH3:1][CH:2]([CH3:3])[N-:4][CH:5]([CH3:6])[CH3:7].[Li+:8]>>[CH3:1][CH:2]([CH3:3])[NH:4][CH:5]([CH3:6])[CH3:7].[Li:8][CH2:9][CH2:10][CH2:11][CH3:12] | C1CCOC1.CC(C)[N-]C(C)C.[Li+] | CC(C)NC(C)C.[Li][CH2]CCC | null | null | null | C-C Coupling | OtherReaction | 19d392fe8cff970cc8e72c5d7d0ff0b2d037e95b7480a1fe0f60997eedee8569 | d681570b7dfd2f5a945b9cf900e060ae5d17f1701fd4a724b1020bc1ee425fbd | null | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[N-;H0;D2:8]-[C:9](-[C;D1;H3:10])-[C;D1;H3:11].[Li+;H0;D0:12]>>[C;D1;H3:5]-[C:6](-[C;D1;H3:7])-[NH;D2;+0:8]-[C:9](-[C;D1;H3:10])-[C;D1;H3:11].[CH3;D1;+0:3]-[CH2;D2;+0:4]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[Li;H0;D1;+0:12] | null | [] | null | null | null | null | A mixture of 10 mmole of lithium diisopropylamide (LDA), formed from n-butyllithium and diisopropylamine, in 10 mL of tetrahydrofuran was cooled to -78° C. Then 2 g of α-isopropyl-3,4-dimethoxybenzyl nitrile was added to the mixture. The reaction mixture was stirred at -78° C. for 20 minutes, 0.78 mL of epibromohydrin ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary amine.Alkyl lithium | C1CCOC1 | null | null | Other | null | null | null | C1CCOC1.CC(C)[N-]C(C)C.[Li+]>>CC(C)NC(C)C.[Li][CH2]CCC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-dcb6757025c842f682ae2753a298d10d | [F][Sb-]([F])([F])([F])([F])[F]>>[F][Sb-]([F])([F])([F])([F])[F] | F[B-](F)(F)F.CC1=CC=C(C[S+](CC2=CC=C(C=C2)C)CC2=CC=C(C=C2)C)C=C1.F[Sb-](F)(F)(F)(F)F.[Na+]>>F[Sb-](F)(F)(F)(F)F.CC1=CC=C(C[S+](CC2=CC=C(C=C2)C)CC2=CC=C(C=C2)C)C=C1 | [F:26][Sb-:27]([F:28])([F:29])([F:30])([F:31])[F:32]>>[F:26][Sb-:27]([F:28])([F:29])([F:30])([F:31])[F:32] | [F][Sb-]([F])([F])([F])([F])[F] | [F][Sb-]([F])([F])([F])([F])[F] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 87.3 | [{"value": 87.0, "product": "F[Sb-](F)(F)(F)(F)F.CC1=CC=C(C[S+](CC2=CC=C(C=C2)C)CC2=CC=C(C=C2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "F[Sb-](F)(F)(F)(F)F.CC1=CC=C(C[S+](CC2=CC=C(C=C2)C)CC2=CC=C(C=C2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Analogously to Example 4c), 100 g (230 mmol) of tris(p-methylbenzyl)sulfonium tetrafluoroborate are reacted with 119.0 g (460 mmol) of sodium hexafluoroantimonate. Recrystallization in isopropanol gives 117.1 g (87% of theory) of tris(p-methylbenzyl)sulfonium hexafluoroantimonate in the form of white crystals of meltin... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [F][Sb-]([F])([F])([F])([F])[F]>>[F][Sb-]([F])([F])([F])([F])[F] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-36a943ae44634d7499c53401c1d522ef | ClCc1c(Cl)cccc1Cl.[S-2]>>Clc1cccc(Cl)c1CSCc1c(Cl)cccc1Cl | [S-2].[Na+].[Na+].ClC1=C(CCl)C(=CC=C1)Cl>>ClC1=C(CSCC2=C(C=CC=C2Cl)Cl)C(=CC=C1)Cl | [Cl:1][c:2]1[cH:5][cH:4][cH:17][c:16]([Cl:7])[c:12]1[CH2:11][Cl:14].[S-2:10]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[CH2:9][S:10][CH2:11][c:12]1[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]1[Cl:19] | ClCc1c(Cl)cccc1Cl.[S-2] | Clc1cccc(Cl)c1CSCc1c(Cl)cccc1Cl | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | O | Aromatic Heterocycle Formation | OtherReaction | bbd8d797677cc7a4d7187a718312fa2016ddacd2e4ab5308eb800d3268288010 | 7ba4a4f3f31ae8886286432e6579c64ca675916874e2a06bb046b80ca16dc3ec | c1ccc(CSCc2ccccc2)cc1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[Cl;H0;D1;+0:7]):[c;H0;D3;+0:8]:1-[CH2;D2;+0:9]-[Cl;H0;D1;+0:10].[S-2;H0;D0:11]>>[Cl;D1;H0:12]-[c:13]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:14]:[c:15](-[Cl;H0;D1;+0:10]):[c;H0;D3;+0:8]:1-[CH2;D2;+0:9]-[S;H0;D2;+0:11]-[C:16]-[c:17]1:[c:18](-[Cl;... | 80.4 | [{"value": 80.0, "product": "ClC1=C(CSCC2=C(C=CC=C2Cl)Cl)C(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "ClC1=C(CSCC2=C(C=CC=C2Cl)Cl)C(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 98.8 g (0.411 mol) of sodium sulfide, 5.0 g of tetrabutylammonium hydrogen sulfate and 110 ml of water are stirred in a reaction vessel equipped with a stirrer, thermometer and heatable dropping funnel, until a solution is obtained. 107.2 g of melted 2,6-dichlorobenzyl chloride are added with vigorous stir... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary halide | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Monosulfide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O | null | null | ClCc1c(Cl)cccc1Cl.[S-2]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O>Clc1cccc(Cl)c1CSCc1c(Cl)cccc1Cl |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9a41d47d8cd54b8b9634060259a56c3c | [F][Sb-]([F])([F])([F])([F])[F]>>[F][Sb-]([F])([F])([F])([F])[F] | F[B-](F)(F)F.ClC1=C(C[S+](CC2=C(C=CC=C2Cl)Cl)CC2=C(C=CC=C2Cl)Cl)C(=CC=C1)Cl.F[Sb-](F)(F)(F)(F)F.[Na+]>>F[Sb-](F)(F)(F)(F)F.ClC1=C(C[S+](CC2=C(C=CC=C2Cl)Cl)CC2=C(C=CC=C2Cl)Cl)C(=CC=C1)Cl | [F:29][Sb-:30]([F:31])([F:32])([F:33])([F:34])[F:35]>>[F:29][Sb-:30]([F:31])([F:32])([F:33])([F:34])[F:35] | [F][Sb-]([F])([F])([F])([F])[F] | [F][Sb-]([F])([F])([F])([F])[F] | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 67.4 | [{"value": 67.4, "product": "F[Sb-](F)(F)(F)(F)F.ClC1=C(C[S+](CC2=C(C=CC=C2Cl)Cl)CC2=C(C=CC=C2Cl)Cl)C(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | null | null | A mixture of 15.0 g (25 mmol) of tris(2,6-dichlorobenzyl)sulfonium tetrafluoroborate in 250 ml of methylene chloride is stirred in a 3-necked flask at about 30° C., until a solution is obtained, and then reacted with sodium hexafluoroantimonate at RT as in Example 9c). Workup of the reaction mixture according to Exampl... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)Cl | 30 | null | [F][Sb-]([F])([F])([F])([F])[F]>C(Cl)Cl>[F][Sb-]([F])([F])([F])([F])[F] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-97f55f6466014133b0ecc5caef9de86e | Clc1ccc(CSc2ccc(Cl)cc2)cc1.OCc1ccc(Cl)cc1>>Clc1ccc(C[S+](Cc2ccc(Cl)cc2)c2ccc(Cl)cc2)cc1 | ClC1=CC=C(CSC2=CC=C(C=C2)Cl)C=C1.ClC1=CC=C(CO)C=C1.[H+].[B-](F)(F)(F)F>>F[B-](F)(F)F.ClC1=CC=C(C=C1)[S+](CC1=CC=C(C=C1)Cl)CC1=CC=C(C=C1)Cl | [Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][S:7][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[cH:23][cH:24]1.O[CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][S+:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:2... | Clc1ccc(CSc2ccc(Cl)cc2)cc1.OCc1ccc(Cl)cc1 | Clc1ccc(C[S+](Cc2ccc(Cl)cc2)c2ccc(Cl)cc2)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 90acb5016cdb3c4f70a53f9624fcd1d38cace5839dd559163e16a03faeda6405 | 4916d5df278cf6cbaf879e5171da5a5b69d2a2f0b6384c34aecd019d644ad325 | c1ccc(C[S+](Cc2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[c:6](-[S;H0;D2;+0:7]-[C:8]-[c:9]):[c:10]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S+;H0;D3:7](-[C:8]-[c:9])-[c:6](:[c:5]):[c:10]):[c:4] | 77.4 | [{"value": 77.4, "product": "F[B-](F)(F)F.ClC1=CC=C(C=C1)[S+](CC1=CC=C(C=C1)Cl)CC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "F[B-](F)(F)F.ClC1=CC=C(C=C1)[S+](CC1=CC=C(C=C1)Cl)CC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.2 g (19.4 mmol) of 4-chlorophenyl 4-chlorobenzyl sulfide, 4.14 g (29.0 mmol) of 4-chlorobenzyl alcohol and 14.15 g (87 mmol) of hydrogen tetrafluoroborate (54% in diethyl ether) in 20 ml of methylene chloride are reacted as in Example 6a) to give 7.23 g (77.4% of theory) of 4-chlorophenylbis(4-chlorobenzyl)sulfonium ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Monosulfide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | Clc1ccc(CSc2ccc(Cl)cc2)cc1.OCc1ccc(Cl)cc1>C(Cl)Cl>Clc1ccc(C[S+](Cc2ccc(Cl)cc2)c2ccc(Cl)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b72b1df24dfd40c49dba15fa1f93e2ed | c1ccc2c(CSCc3cccc4ccccc34)cccc2c1>>CC[S+](Cc1cccc2ccccc12)Cc1cccc2ccccc12 | C1(=CC=CC2=CC=CC=C12)CSCC1=CC=CC2=CC=CC=C12.F[Sb-](F)(F)(F)(F)F.C(C)[O+](CC)CC>>F[Sb-](F)(F)(F)(F)F.C1(=CC=CC2=CC=CC=C12)C[S+](CC)CC1=CC=CC2=CC=CC=C12 | [S:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[CH2:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12>>[CH3:1][CH2:2][S+:3]([CH2:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)[CH2:15][c:16]1[cH:17][cH:18][cH:19][c:20]2[cH:21][cH:22][cH:23]... | c1ccc2c(CSCc3cccc4ccccc34)cccc2c1 | CC[S+](Cc1cccc2ccccc12)Cc1cccc2ccccc12 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | ffcc210dc3e2d060068e17fbcbb6378cb0ec116a6dbcbb99fb3a863b3f527b24 | b54e03cebd44ff29798a9f8438f45b03dda0927a86d16a58dd3a447f535e1302 | c1ccc2c(C[SH+]Cc3cccc4ccccc34)cccc2c1 | [c:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[c:5]>>[C;D1;H3:6]-[C:7]-[S+;H0;D3:3](-[C:2]-[c:1])-[C:4]-[c:5] | 98.5 | [{"value": 98.0, "product": "F[Sb-](F)(F)(F)(F)F.C1(=CC=CC2=CC=CC=C12)C[S+](CC)CC1=CC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "F[Sb-](F)(F)(F)(F)F.C1(=CC=CC2=CC=CC=C12)C[S+](CC)CC1=CC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5.0 g (15.9 mmol) of bis(1-naphthylmethyl) sulfide and 5.93 g (17.5 mmol) of triethyloxonium hexafluoroantimonate in 30 ml of methylene chloride are reacted according to Example 1a) to give 9.07 g (98% of theory) of bis(1-naphthylmethyl)ethylsulfonium hexafluoroantimonate in the form of white crystals of melting point ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | null | null | c1ccc2ccccc2c1.c1ccc2ccccc2c1 | null | C(Cl)Cl | null | null | c1ccc2c(CSCc3cccc4ccccc34)cccc2c1>C(Cl)Cl>CC[S+](Cc1cccc2ccccc12)Cc1cccc2ccccc12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9ec0a0a647af429cbc50491e9b181fb6 | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12>>CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](N)C(=O)N12 | CO.P(Cl)(Cl)(Cl)(Cl)Cl.O=C1O[C@@H](CC1)C=1CS[C@H]2N(C1C(=O)OC(C)(C)C)C([C@H]2NC(COC2=CC=CC=C2)=O)=O.CN1CCOCC1>>N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O | O=C(COc1ccccc1)[NH:20][C@H:19]1[C@H:18]2[S:17][CH2:16][C:9]([C@@H:10]3[CH2:11][CH2:12][C:13](=[O:14])[O:15]3)=[C:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[N:23]2[C:21]1=[O:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C:8]1=[C:9]([C@@H:10]2[CH2:11][CH2:12][C:13](=[O:14])[O:15]2)[CH2:16][S:17][C@@H:18... | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12 | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](N)C(=O)N12 | null | null | ClCCl.O | Reduction | Hydrogenolysis of amides/imides/carbamates | 9b32bac95ab636d62481cab1eb45262663bda67c3b4ed47149087265cf7e9b08 | 69ea9c3b2c146d1c3379cd65b32d2668309ecd44d0c250c9b4680c17644f9952 | O=C1CC[C@@H](C2=CN3C(=O)C[C@H]3SC2)O1 | O=C(-C-O-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]1-[C:3](-[#16:4])-[#7:5](-[C:6]-1=[O;D1;H0:7])-[C:8](-[C:9](-[#8:10])=[O;D1;H0:11])=[C:12]>>[#16:4]-[C:3]1-[#7:5](-[C:6](=[O;D1;H0:7])-[C:2]-1-[NH2;D1;+0:1])-[C:8](-[C:9](-[#8:10])=[O;D1;H0:11])=[C:12] | 40.1 | [{"value": 40.0, "product": "N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.1, "product": "N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 0.75 | HOUR | Phosphorus pentachloride (0.35 g,1.7 mmol) in dichloromethane (9 ml) was added to t-butyl (6R,7R)-3-[(5S)-2-oxotetrahydrofuran-5-yl]-7-phenoxyacetamido-ceph-3-em-4-carboxylate (0.526 g, 1.1 mmol) and N-methylmorpholine (0.24 ml, 2.2 mmol) in dichloromethane (15 ml) at <-20° C. The reaction was stirred at -15±5° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Primary amine | c1ccccc1 | null | C1CCOC1.C1=CN2CC[C@H]2SC1 | HO- | ClCCl.O | -15 | 0.75 | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12>ClCCl.O>CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](N)C(=O)N12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-aaa752085c62402d8beb5b3c0698a75a | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](N)C(=O)N12.CO/N=C(\C(=O)[O-])c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>>CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)(C)C)=C([C@@H]3CCC(=O)O3)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | CS(=O)(=O)Cl.CO\N=C(/C(=O)[O-])\C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[Na+].N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O.N1=CC=CC=C1>>CO\N=C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O)\C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | [NH2:7][C@@H:8]1[C:9](=[O:10])[N:11]2[C:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[C:20]([C@@H:21]3[CH2:22][CH2:23][C:24](=[O:25])[O:26]3)[CH2:27][S:28][C@H:29]12.[O-][C:5](/[C:4](=[N:3]\[O:2][CH3:1])[c:30]1[cH:31][s:32][c:33]([NH:34][C:35]([c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)([c:42]2[cH:43][... | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](N)C(=O)N12.CO/N=C(\C(=O)[O-])c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)(C)C)=C([C@@H]3CCC(=O)O3)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | OtherReaction | 01b411aa709aa72475efefee2037796aeb41c60940ddba8e15aefc45a95317a8 | 45ca336cc0b18cf59a837ab710e8845f67d23306b24bf1f37b36a34a2de4779a | N=C(C(=O)N[C@@H]1C(=O)N2C=C([C@@H]3CCC(=O)O3)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 | [#16;a:1]:[c:2]:[c:3](/[C:4](=[#7:5]/[#8:6])-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8]):[#7;a:9].[#16:10]-[C:11]1-[#7:12](-[C:13](-[C:14](-[#8:15])=[O;D1;H0:16])=[C:17])-[C:18](=[O;D1;H0:19])-[C:20]-1-[NH2;D1;+0:21]>>[#16:10]-[C:11]1-[#7:12](-[C:13](-[C:14](-[#8:15])=[O;D1;H0:16])=[C:17])-[C:18](=[O;D1;H0:19])-[C:20]-1-[NH;D2;... | 60.1 | [{"value": 60.0, "product": "CO\\N=C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O)\\C=1N=C(SC1)NC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.1, "product": "CO\\N=C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)[C@@H]2CCC(O2)=O)C(=O)OC(C)(C)C)C1=O)\\C=1N=... | -10 | CELSIUS | 1 | HOUR | Methanesulphonyl chloride (23 μl, 0.3 mmol) was added to sodium 2-(Z)-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetate (0.12 g,0.25 mmol) in DMF (0.5 ml) at -40° C. The mixture was allowed to warm to -10° C. over 0.5 h then cooled to -30° C. and t-butyl (6R,7R)-7-amino-3-[(5S)-2-oxotetrahydrofuran-5-yl]ceph-3-em-4-car... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide | null | null | C1=CN2CC[C@H]2SC1.C1CCOC1.c1cscn1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.C(C)(=O)OCC | -10 | 1 | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](N)C(=O)N12.CO/N=C(\C(=O)[O-])c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1>CN(C)C=O.C(C)(=O)OCC>CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OC(C)(C)C)=C([C@@H]3CCC(=O)O3)CS[C@H]12)c1csc(NC(c2ccccc2)(c2ccccc2)c2ccccc2)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-42452324fa004ae9a61634f23f042346 | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](NC(=O)/C(=N\OC(c3ccccc3)(c3ccccc3)c3ccccc3)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12>>Nc1nc(/C(=N/O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(C4CCC(=O)O4)CS[C@H]23)cs1 | O=C1O[C@@H](CC1)C=1CS[C@H]2N(C1C(=O)OC(C)(C)C)C([C@H]2NC(\C(=N/OC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)\C=2N=C(SC2)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=O)=O>>NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C2CCC(O2)=O)C(=O)O)C1=O)=N/O | CC(C)(C)[O:18][C:16]([C:15]1=[C:19]([C@@H:20]2[CH2:21][CH2:22][C:23](=[O:24])[O:25]2)[CH2:26][S:27][C@@H:28]2[C@H:11]([NH:10][C:8](/[C:5]([c:4]3[n:3][c:2]([NH:1]C(c4ccccc4)(c4ccccc4)c4ccccc4)[s:30][cH:29]3)=[N:6]\[O:7]C(c3ccccc3)(c3ccccc3)c3ccccc3)=[O:9])[C:12](=[O:13])[N:14]12)=[O:17]>>[NH2:1][c:2]1[n:3][c:4](/[C:5](=... | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](NC(=O)/C(=N\OC(c3ccccc3)(c3ccccc3)c3ccccc3)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12 | Nc1nc(/C(=N/O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(C4CCC(=O)O4)CS[C@H]23)cs1 | null | null | C(=O)O.Cl | Deprotection | OtherReaction | 9ed8e1c8cd7cab9d2dc852f9cdb655039c4170a109236854e5fa96cd6f3c5a49 | 378a48b297e6ff164c759e3714db3ee80d0500aae73ea764c3540e6da37d81b1 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C3CCC(=O)O3)CS[C@H]12)c1cscn1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5](-[C:6]-[#8:7])-[C:8]-[#16:9])-[#7:10]-[C:11]=[O;D1;H0:12].[#7:13]-[C:14](=[O;D1;H0:15])/[C:16](=[#7:17]\[O;H0;D2;+0:18]-C(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1)-[c:19]1:[#7;a:20]:[c:21](-[NH;D2;+0:22]-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c... | null | [] | null | null | 1 | HOUR | t-Butyl (6R,7R)-3-[(5S)-2-oxotetrahydrofuran-5-yl]-7-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetamido]ceph-3-em-4-carboxylate (0.22 g) was dissolved in 0.1M hydrochloric acid in 90% formic acid (2.5 ml) and stirred for 1 h. Concentrated hydrochloric acid (0.1 ml) was added and stirring was continued for a f... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Boc | Carboxylic acid.Primary amine.Oxime | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | c1cscn1.C1=CN2CC[C@H]2SC1.C1CCOC1 | Other | C(=O)O.Cl | null | 1 | CC(C)(C)OC(=O)C1=C([C@@H]2CCC(=O)O2)CS[C@@H]2[C@H](NC(=O)/C(=N\OC(c3ccccc3)(c3ccccc3)c3ccccc3)c3csc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)n3)C(=O)N12>C(=O)O.Cl>Nc1nc(/C(=N/O)C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(C4CCC(=O)O4)CS[C@H]23)cs1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-377f08373f404f4f90d97a6cafb8213b | CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1S.O=C1CC(C(=O)CCl)CO1>>CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1SCC(=O)C1COC(=O)C1 | ClCC(=O)C1CC(OC1)=O.C([O-])([O-])=O.[K+].[K+].OC(C(=O)OC(C)(C)C)N1C([C@H]([C@H]1S)NC(COC1=CC=CC=C1)=O)=O>>OC(C(=O)OC(C)(C)C)N1C([C@H]([C@H]1SCC(=O)C1CC(OC1)=O)NC(COC1=CC=CC=C1)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([OH:9])[N:10]1[C:11](=[O:12])[C@@H:13]([NH:14][C:15](=[O:16])[CH2:17][O:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[C@H:25]1[SH:26].Cl[CH2:27][C:28](=[O:29])[CH:30]1[CH2:31][O:32][C:33](=[O:34])[CH2:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]([... | CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1S.O=C1CC(C(=O)CCl)CO1 | CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1SCC(=O)C1COC(=O)C1 | null | null | C(C)(=O)OCC.CC(=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 2832b2abe2c6eec311e6ff681a4a2f4badad287d4aa9571a0c5dd65e244d2fb1 | fd33520d014e32be1d226bbdf70688fb706406f9aa3166008d4e284419b90a27 | O=C(COc1ccccc1)N[C@@H]1C(=O)N[C@@H]1SCC(=O)C1COC(=O)C1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]1-[C:10](=[O;D1;H0:11])-[C:12]-[C:13]-1-[SH;D1;+0:14]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]-[#7:9]1-[C:10](=[O;D1;H0:11])-[C:12]-[C:13]-1-[S;H0;D2;+0:14]-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4] | 68 | [{"value": 68.0, "product": "OC(C(=O)OC(C)(C)C)N1C([C@H]([C@H]1SCC(=O)C1CC(OC1)=O)NC(COC1=CC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "OC(C(=O)OC(C)(C)C)N1C([C@H]([C@H]1SCC(=O)C1CC(OC1)=O)NC(COC1=CC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | (RS)-4-Chloroacetyltetrahydrofuran-2-one (2.060 g, 12.6 mmol), followed by potassium carbonate (0.690 g, 5 mmol) were added to crude t-butyl (2RS)-2-hydroxy-[(3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-on-1-yl]acetate (3.866 g) (prepared as described in Example 1c) in acetone (10 ml). The reaction was stirred 1 h. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aliphatic thiol | Ketone.Monosulfide | null | null | C1C[NH]C1.c1ccccc1.C1CCOC1 | HCl | C(C)(=O)OCC.CC(=O)C | null | 1 | CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1S.O=C1CC(C(=O)CCl)CO1>C(C)(=O)OCC.CC(=O)C>CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1SCC(=O)C1COC(=O)C1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4d70e3eec3d34997a22908f6fa4984e9 | CC(C)(C)OC(=O)C1=C(C2COC(=O)C2)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12>>CC(C)(C)OC(=O)C1=C(C2COC(=O)C2)CS[C@@H]2[C@H](N)C(=O)N12 | CO.P(Cl)(Cl)(Cl)(Cl)Cl.O=C1OCC(C1)C=1CS[C@H]2N(C1C(=O)OC(C)(C)C)C([C@H]2NC(COC2=CC=CC=C2)=O)=O.CN1CCOCC1>>N[C@H]1[C@@H]2N(C(=C(CS2)C2CC(OC2)=O)C(=O)OC(C)(C)C)C1=O | O=C(COc1ccccc1)[NH:20][C@H:19]1[C@H:18]2[S:17][CH2:16][C:9]([CH:10]3[CH2:11][O:12][C:13](=[O:14])[CH2:15]3)=[C:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[N:23]2[C:21]1=[O:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[C:8]1=[C:9]([CH:10]2[CH2:11][O:12][C:13](=[O:14])[CH2:15]2)[CH2:16][S:17][C@@H:18]2[C... | CC(C)(C)OC(=O)C1=C(C2COC(=O)C2)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12 | CC(C)(C)OC(=O)C1=C(C2COC(=O)C2)CS[C@@H]2[C@H](N)C(=O)N12 | null | null | ClCCl.O | Reduction | Hydrogenolysis of amides/imides/carbamates | 9b32bac95ab636d62481cab1eb45262663bda67c3b4ed47149087265cf7e9b08 | 69ea9c3b2c146d1c3379cd65b32d2668309ecd44d0c250c9b4680c17644f9952 | O=C1CC(C2=CN3C(=O)C[C@H]3SC2)CO1 | O=C(-C-O-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]1-[C:3](-[#16:4])-[#7:5](-[C:6]-1=[O;D1;H0:7])-[C:8](-[C:9](-[#8:10])=[O;D1;H0:11])=[C:12]>>[#16:4]-[C:3]1-[#7:5](-[C:6](=[O;D1;H0:7])-[C:2]-1-[NH2;D1;+0:1])-[C:8](-[C:9](-[#8:10])=[O;D1;H0:11])=[C:12] | 29.4 | [{"value": 29.0, "product": "N[C@H]1[C@@H]2N(C(=C(CS2)C2CC(OC2)=O)C(=O)OC(C)(C)C)C1=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.4, "product": "N[C@H]1[C@@H]2N(C(=C(CS2)C2CC(OC2)=O)C(=O)OC(C)(C)C)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of phosphorous pentachloride (0.380 g, 1.8 mmol) in dichloromethane (9.5 ml) was added to t-butyl (6R,7R)-3-[(4RS)-2-oxotetrahydrofuran-4-yl]-7-phenoxyacetamidoceph-3-em-4-carboxylate (0.554 g, 1.2 mmol) and N-methylmorpholine (265 μh, 2.4 mmol) in dichloromethane (15 ml) at <-20° C. under argon. Stirred 0.5... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amide | Primary amine | c1ccccc1 | null | C1CCOC1.C1=CN2CC[C@H]2SC1 | HO- | ClCCl.O | null | 0.5 | CC(C)(C)OC(=O)C1=C(C2COC(=O)C2)CS[C@@H]2[C@H](NC(=O)COc3ccccc3)C(=O)N12>ClCCl.O>CC(C)(C)OC(=O)C1=C(C2COC(=O)C2)CS[C@@H]2[C@H](N)C(=O)N12 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-25dcd8cb6bae4c88a76e6afa5f16ed75 | CC(C)(C)C(=O)OCBr.CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C3CCC(=O)O3)CS[C@H]12)c1csc(N)n1>>CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OCOC(=O)C(C)(C)C)=C(C3CCC(=O)O3)CS[C@H]12)c1csc(N)n1 | C(C(C)(C)C)(=O)OCBr.[I-].[Na+].[I-].NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C2CCC(O2)=O)C(=O)[O-])C1=O)=N/OC.[Na+]>>NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C2CCC(O2)=O)C(=O)OCOC(C(C)(C)C)=O)C1=O)=N/OC | Br[CH2:16][O:17][C:18](=[O:19])[C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2]/[N:3]=[C:4](\[C:5](=[O:6])[NH:7][C@@H:8]1[C:9](=[O:10])[N:11]2[C:12]([C:13](=[O:14])[O-:15])=[C:24]([CH:25]3[CH2:26][CH2:27][C:28](=[O:29])[O:30]3)[CH2:31][S:32][C@H:33]12)[c:34]1[cH:35][s:36][c:37]([NH2:38])[n:39]1>>[CH3:1][O:2]/[N:3]=[C:4]... | CC(C)(C)C(=O)OCBr.CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C3CCC(=O)O3)CS[C@H]12)c1csc(N)n1 | CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OCOC(=O)C(C)(C)C)=C(C3CCC(=O)O3)CS[C@H]12)c1csc(N)n1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC.CC(=O)C.CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | cc1d4e55611fe4d93ec51a6560b7681a6437fcff8318e73cf7c223359a8b5862 | 9a5997b9aa50a69ce330b8e8c103cdd0752c17ab18e906e2de9560f67bea2bb1 | N=C(C(=O)N[C@@H]1C(=O)N2C=C(C3CCC(=O)O3)CS[C@H]12)c1cscn1 | Br-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[#16:6]-[C:7]-[C:8](-[C:9]-[#8:10])=[C:11](-[C:12](-[O-;H0;D1:13])=[O;D1;H0:14])-[#7:15]-[C:16]=[O;D1;H0:17]>>[#16:6]-[C:7]-[C:8](-[C:9]-[#8:10])=[C:11](-[C:12](=[O;D1;H0:14])-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[#7:15]-[C:16]=[O;D1;H0:17] | 59.1 | [{"value": 59.0, "product": "NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C2CCC(O2)=O)C(=O)OCOC(C(C)(C)C)=O)C1=O)=N/OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.1, "product": "NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)C2CCC(O2)=O)C(=O)OCOC(C(C)(C)C)=O)C1=O)=N/OC", "details": "CALCULATEDPERCEN... | null | null | 0.5 | HOUR | Pivaloyloxymethyl bromide (0.10 g, ca. 0.5 mmol) and sodium iodide (0.1 g) in acetone (1 ml) were stirred for 0.25 h, filtered and evaporated in vacuo. The iodide in toluene (0.5 ml) was added to sodium (6R,7R)-7-[2(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(5RS)-2-oxotetrahydrofuran-5-yl]ceph-3-em-4-carboxy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Ester | null | null | C1=CN2CC[C@H]2SC1.C1CCOC1.c1cscn1 | Br- | C1(=CC=CC=C1)C.C(C)(=O)OCC.CC(=O)C.CN1C(CCC1)=O | null | 0.5 | CC(C)(C)C(=O)OCBr.CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C3CCC(=O)O3)CS[C@H]12)c1csc(N)n1>C1(=CC=CC=C1)C.C(C)(=O)OCC.CC(=O)C.CN1C(CCC1)=O>CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)OCOC(=O)C(C)(C)C)=C(C3CCC(=O)O3)CS[C@H]12)c1csc(N)n1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9f0b3ad6f04142c8a878ebd3b7343915 | CC(C)(C)[Si](C)(C)OCc1cccc(COC(=N)C(Cl)(Cl)Cl)c1.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(OCc4cccc(CO[Si](C)(C)C(C)(C)C)c4)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC)C)C)O[Si](C)(C)C(C)(C)C)=O.ClC(C(OCC1=CC(=CC=C1)CO[Si](C)(C)C(C)(C)C)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OCC2=CC(=CC=C2)CO[Si](C)(C)C(C... | N=C(O[CH2:40][c:41]1[cH:42][cH:43][cH:44][c:45]([CH2:46][O:47][Si:48]([CH3:49])([CH3:50])[C:51]([CH3:52])([CH3:53])[CH3:54])[cH:55]1)C(Cl)(Cl)Cl.[CH3:1][CH2:2][CH:3]1[CH:4]=[C:5]([CH3:6])[CH2:7][CH:8]([CH3:9])[CH2:10][CH:11]([O:12][CH3:13])[CH:14]2[O:15][C:16]([OH:17])([C:18](=[O:19])[C:20](=[O:21])[N:22]3[CH2:23][CH2:... | CC(C)(C)[Si](C)(C)OCc1cccc(COC(=N)C(Cl)(Cl)Cl)c1.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(OCc4cccc(CO[Si](C)(C)C(C)(C)C)c4)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e1602c7639e9590c57e1f519302834b854314fa06b50f2e00792e7923548c28a | 9939e71487b269001d097fe9b7393354dcb141bf54208fca597f111e50af4454 | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCC(OCc3ccccc3)CC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8] | null | [] | null | null | null | null | To a solution of 17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (230 mg in 3 ml 33% methylene chloride in cyclohexane) was added m-(tert-butyldimeth... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol | Ether | null | null | C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2.C1CCCCC1.c1ccccc1 | HCl | null | null | null | CC(C)(C)[Si](C)(C)OCc1cccc(COC(=N)C(Cl)(Cl)Cl)c1.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(OCc4cccc(CO[Si](C)(C)C(C)(C)C)c4)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-2829dc3737ff47048b1cc81ac4786723 | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC>>C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CC1OC | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC)C)C)O)=O.ClC(C(OCC=C)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OCC=C)OC)C)C)O)=O | N=C(O[CH2:3][CH:2]=[CH2:1])C(Cl)(Cl)Cl.[OH:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH:12]2[O:13][C:14](=[O:15])[CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:23])[C:24](=[O:25])[C:26]3([OH:27])[O:28][CH:29]([CH:30]([O:31][CH3:32])[CH2:33][CH:34]([CH3:35])[CH2:36][C:37]([CH3:38])=[CH:39][CH:40](... | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CC1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5e0bd280477912044021df5d3fd2ce4d771142c5c1d73d2ffdc58062781db2ee | 98e8b054881a6dc34d0a4fbf61a0ec3e2665076eb1dc46f33e0abb14bb07b5ea | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:7] | null | [] | null | null | null | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (200 mg in 3.0 ml 33% methylene chloride in cyclohexane), allyl trichloroacetimidate (88 μl neat) was added a... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol.Allyl | Ether | null | null | C1CCCCC1.C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2 | HCl | null | null | null | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC>>C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CC1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-d7c1b30b953d4044ac31206c04713573 | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC>>C=CCOC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)O)C)C)O)=O.ClC(C(OCC=C)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OCC=C)C)C)O)=O | N=C(O[CH2:3][CH:2]=[CH2:1])C(Cl)(Cl)Cl.[OH:4][CH:5]1[CH2:6][CH:7]([CH:8]=[C:9]([CH3:10])[CH:11]2[O:12][C:13](=[O:14])[CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:21](=[O:22])[C:23](=[O:24])[C:25]3([OH:26])[O:27][CH:28]([CH:29]([O:30][CH3:31])[CH2:32][CH:33]([CH3:34])[CH2:35][C:36]([CH3:37])=[CH:38][CH:39]([CH2:40]... | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC | C=CCOC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5e0bd280477912044021df5d3fd2ce4d771142c5c1d73d2ffdc58062781db2ee | 98e8b054881a6dc34d0a4fbf61a0ec3e2665076eb1dc46f33e0abb14bb07b5ea | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:7] | null | [] | null | null | null | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(3",4 "-dihydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (100 mg in 1.5 ml 33% methylene chlorine in cyclohexane), allyl trichloroacetimidate (53 μl neat) was added and th... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol.Allyl | Ether | null | null | C1CCCCC1.C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2 | HCl | null | null | null | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC>>C=CCOC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-c6c01f0af21146f0824d7218b94b67f9 | CC(C)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC(C)C)C3)C(C)C(O)CC1=O)C(C)CC2OC | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)O)C)C)O)=O.ClC(C(OC(C)C)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC(C)C)C)C)O)=O | N=C(O[CH:42]([CH3:43])[CH3:44])C(Cl)(Cl)Cl.[CH3:1][CH2:2][CH:3]1[CH:4]=[C:5]([CH3:6])[CH2:7][CH:8]([CH3:9])[CH2:10][CH:11]([O:12][CH3:13])[CH:14]2[O:15][C:16]([OH:17])([C:18](=[O:19])[C:20](=[O:21])[N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]3[C:28](=[O:29])[O:30][CH:31]([C:32]([CH3:33])=[CH:34][CH:35]3[CH2:36][CH2:3... | CC(C)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC(C)C)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e1602c7639e9590c57e1f519302834b854314fa06b50f2e00792e7923548c28a | 9939e71487b269001d097fe9b7393354dcb141bf54208fca597f111e50af4454 | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7] | null | [] | null | null | null | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (110 mg in 1.5 ml 33% methylene chloride in cyclohexane), isopropyl trichloroacetimidate (52 μl neat) was added and... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol | Ether | null | null | C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2.C1CCCCC1 | HCl | null | null | null | CC(C)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC(C)C)C3)C(C)C(O)CC1=O)C(C)CC2OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-308d9da7373444b7b9987e33d7c0ad68 | CC(C)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)CCC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC(C)C)C3)C(C)CCC1=O)C(C)CC2OC | C(C)C1C(CCC(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)O)C)C)=O.ClC(C(OC(C)C)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CCC(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC(C)C)C)C)=O | N=C(O[CH:42]([CH3:43])[CH3:44])C(Cl)(Cl)Cl.[CH3:1][CH2:2][CH:3]1[CH:4]=[C:5]([CH3:6])[CH2:7][CH:8]([CH3:9])[CH2:10][CH:11]([O:12][CH3:13])[CH:14]2[O:15][C:16]([OH:17])([C:18](=[O:19])[C:20](=[O:21])[N:22]3[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]3[C:28](=[O:29])[O:30][CH:31]([C:32]([CH3:33])=[CH:34][CH:35]3[CH2:36][CH2:3... | CC(C)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)CCC1=O)C(C)CC2OC | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC(C)C)C3)C(C)CCC1=O)C(C)CC2OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e1602c7639e9590c57e1f519302834b854314fa06b50f2e00792e7923548c28a | 9939e71487b269001d097fe9b7393354dcb141bf54208fca597f111e50af4454 | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7] | null | [] | null | null | null | null | To a solution of 17-ethyl-1-hydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (69 mg in 3 ml 33% methylene chloride in cyclohexane), isopropyl trichloroacetimidate (22 μl neat) was added and the rea... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol | Ether | null | null | C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2.C1CCCCC1 | HCl | null | null | null | CC(C)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)CCC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC(C)C)C3)C(C)CCC1=O)C(C)CC2OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-bf49a5d763df43bbb664004278818861 | C=C(CC)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC>>C=C(CC)OC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)O)C)C)O)=O.ClC(C(OC(=C)CC)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC(=C)CC)C)C)O)=O | N=C(C(Cl)(Cl)Cl)[O:5][C:2](=[CH2:1])[CH2:3][CH3:4].O[CH:6]1[CH2:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH:12]2[O:13][C:14](=[O:15])[CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:23])[C:24](=[O:25])[C:26]3([OH:27])[O:28][CH:29]([CH:30]([O:31][CH3:32])[CH2:33][CH:34]([CH3:35])[CH2:36][C:37]([CH3:38])=[CH:39][CH:40](... | C=C(CC)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC | C=C(CC)OC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 94728dc822682637d74bb4894b895168d7b3c482232fd16deb2c4e4e65588337 | 9939e71487b269001d097fe9b7393354dcb141bf54208fca597f111e50af4454 | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4].O-[CH;D3;+0:5](-[C:6]-[C:7]-[C:8]=[C:9])-[C:10](-[O;D1;H1:11])-[C:12]>>[C:9]=[C:8]-[C:7]-[C:6]-[CH;D3;+0:5](-[O;H0;D2;+0:1]-[C:2](-[C:3])=[C;D1;H2:4])-[C:10](-[O;D1;H1:11])-[C:12] | null | [] | null | null | null | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(3",4"-dihydroxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (150 mg in 3 ml 33% methylene chloride in cyclohexane), sec-butenyl trichloroacetimidate (62 μl neat) was added and... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol | Ether | C1CCCCC1 | C1CCCCC1 | C1CCCCC1.C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2 | HCl | null | null | null | C=C(CC)OC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(O)C3)C(C)C(O)CC1=O)C(C)CC2OC>>C=C(CC)OC1CC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O)C2C)C(OC)CC3C)CCC1O |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3a286637eb6144d3b0fd9d7bee18976c | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O[Si](C)(C)C(C)(C)C)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O[Si](C)(C)C(C)(C)C)OC)C)C)O[Si](C)(C)C(C)(C)C)=O.F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC)C)C)O[Si](C)(C)C(C)(C)C)=O | CC(C)(C)[Si](C)(C)[O:39][CH:38]1[CH2:37][CH2:36][CH:35]([CH:34]=[C:32]([CH:31]2[O:30][C:28](=[O:29])[CH:27]3[N:22]([C:20](=[O:21])[C:18](=[O:19])[C:16]4([OH:17])[O:15][CH:14]([CH:11]([O:12][CH3:13])[CH2:10][CH:8]([CH3:9])[CH2:7][C:5]([CH3:6])=[CH:4][CH:3]([CH2:2][CH3:1])[C:56](=[O:57])[CH2:55][CH:46]([O:47][Si:48]([CH3... | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O[Si](C)(C)C(C)(C)C)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | null | null | C(C)#N.C(C)(=O)OCC | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4] | 58.4 | [{"value": 58.4, "product": "C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC)C)C)O[Si](C)(C)C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(tert-butyldimethylsiloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (2.91 g) in acetonitrile (15 ml) was added a solution of 2% hydro... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2.C1CCCCC1 | Other | C(C)#N.C(C)(=O)OCC | null | 4 | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O[Si](C)(C)C(C)(C)C)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC>C(C)#N.C(C)(=O)OCC>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-147153a83520490d864abe1bde456d6b | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC>>C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O[Si](C)(C)C(C)(C)C)C2C)C(OC)CC3C)CC1OC | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC)C)C)O[Si](C)(C)C(C)(C)C)=O.C(C=C)OC(C(Cl)(Cl)Cl)=N.C1CCCCC1.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OCC=C)OC)C)C)O[Si](C)(C)C(C)(C)C)=O | N=C(O[CH2:3][CH:2]=[CH2:1])C(Cl)(Cl)Cl.[OH:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH:12]2[O:13][C:14](=[O:15])[CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:23])[C:24](=[O:25])[C:26]3([OH:27])[O:28][CH:29]([CH:30]([O:31][CH3:32])[CH2:33][CH:34]([CH3:35])[CH2:36][C:37]([CH3:38])=[CH:39][CH:40](... | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC | C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O[Si](C)(C)C(C)(C)C)C2C)C(OC)CC3C)CC1OC | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 5e0bd280477912044021df5d3fd2ce4d771142c5c1d73d2ffdc58062781db2ee | 98e8b054881a6dc34d0a4fbf61a0ec3e2665076eb1dc46f33e0abb14bb07b5ea | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:7] | null | [] | null | null | null | null | To a solution of 17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (820 mg in 9 ml 33% methylene chloride in cyclohexane allyl trichloroacetimidate (36... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol.Allyl | Ether | null | null | C1CCCCC1.C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2 | HCl | C(Cl)Cl | null | null | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)C(O[Si](C)(C)C(C)(C)C)CC1=O)C(C)CC2OC>C(Cl)Cl>C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CC(O[Si](C)(C)C(C)(C)C)C2C)C(OC)CC3C)CC1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-48d1ccd4361a46e4a777805b0cd9bb87 | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)CCC1=O)C(C)CC2OC>>C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CCC2C)C(OC)CC3C)CC1OC | C(C)C1C(CCC(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)O)OC)C)C)=O.ClC(C(OCC=C)=N)(Cl)Cl.FC(S(=O)(=O)O)(F)F>>C(C)C1C(CCC(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OCC=C)OC)C)C)=O | N=C(O[CH2:3][CH:2]=[CH2:1])C(Cl)(Cl)Cl.[OH:4][CH:5]1[CH2:6][CH2:7][CH:8]([CH:9]=[C:10]([CH3:11])[CH:12]2[O:13][C:14](=[O:15])[CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:23])[C:24](=[O:25])[C:26]3([OH:27])[O:28][CH:29]([CH:30]([O:31][CH3:32])[CH2:33][CH:34]([CH3:35])[CH2:36][C:37]([CH3:38])=[CH:39][CH:40](... | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)CCC1=O)C(C)CC2OC | C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CCC2C)C(OC)CC3C)CC1OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5e0bd280477912044021df5d3fd2ce4d771142c5c1d73d2ffdc58062781db2ee | 98e8b054881a6dc34d0a4fbf61a0ec3e2665076eb1dc46f33e0abb14bb07b5ea | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCCCC2)CCC1 | Cl-C(-Cl)(-Cl)-C(=N)-O-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3])-[C:7] | null | [] | null | null | null | null | To a solution of 17-ethyl-1-hydroxy-12-[2'-(4"-hydroxy-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (400 mg in 6 ml 33% methylene chloride in cyclohexane), allyl trichloroacetimidate (209 μl neat) was added and the... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ether.Secondary alcohol.Allyl | Ether | null | null | C1CCCCC1.C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2 | HCl | null | null | null | C=CCOC(=N)C(Cl)(Cl)Cl.CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(O)C(OC)C3)C(C)CCC1=O)C(C)CC2OC>>C=CCOC1CCC(C=C(C)C2OC(=O)C3CCCCN3C(=O)C(=O)C3(O)OC(C(OC)CC(C)CC(C)=CC(CC)C(=O)CCC2C)C(OC)CC3C)CC1OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-96c5cacff114416986b9a71bacea67ab | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4cccc(C5OCCO5)c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC>>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4cccc(C=O)c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OC2=CC(=CC=C2)C2OCCO2)OC)C)C)O)=O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OC2=CC(=CC=C2)C=O)OC)C)C)O)=O | C1C[O:46][CH:45]([c:44]2[cH:43][cH:42][cH:41][c:40]([O:39][CH:38]3[CH2:37][CH2:36][CH:35]([CH:34]=[C:32]([CH:31]4[O:30][C:28](=[O:29])[CH:27]5[N:22]([C:20](=[O:21])[C:18](=[O:19])[C:16]6([OH:17])[O:15][CH:14]([CH:11]([O:12][CH3:13])[CH2:10][CH:8]([CH3:9])[CH2:7][C:5]([CH3:6])=[CH:4][CH:3]([CH2:2][CH3:1])[C:57](=[O:58])... | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4cccc(C5OCCO5)c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4cccc(C=O)c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC | null | null | CO | Miscellaneous | Acetal hydrolysis to aldehyde | f12636b09f9df336ccc8fe82b927db0e267bccc7cae0970f1f91c7ceed085225 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C1CC=CCCCCC2CCCC(O2)C(=O)C(=O)N2CCCCC2C(=O)OC(C=CC2CCC(Oc3ccccc3)CC2)CCC1 | [c:1]:[c:2](-[CH;D3;+0:3]1-O-C-C-[O;H0;D2;+0:4]-1):[c:5]>>[O;H0;D1;+0:4]=[CH;D2;+0:3]-[c:2](:[c:1]):[c:5] | 31.5 | [{"value": 31.5, "product": "C(C)C1C(CC(C(C(OC(C2CCCCN2C(C(C2(C(CC(C(C(CC(CC(=C1)C)C)OC)O2)OC)C)O)=O)=O)=O)C(=CC2CC(C(CC2)OC2=CC(=CC=C2)C=O)OC)C)C)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 17-ethyl-1,14-dihydroxy-12-[2'-(4"-(3'"-dioxolanylphenyloxy)-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10,16-tetraone (20 mg in 1 ml methylene chloride) was added 1 ml of a 2.2% solution of p-toluensulfonic a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCO1 | null | C1=CCCCCC2CCCC(CCN3CCCCC3COCCCCCC1)O2.C1CCCCC1.c1ccccc1 | HO- | CO | null | null | CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4cccc(C5OCCO5)c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC>CO>CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C)=CC3CCC(Oc4cccc(C=O)c4)C(OC)C3)C(C)C(O)CC1=O)C(C)CC2OC |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-3c493c10936e478782ba229f94aee306 | O=C([O-])C(=O)[O-].[Co+2].[Y+3]>>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Co+2].[Y+3] | C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+].[N+](=O)([O-])[O-].[Co+2].[N+](=O)([O-])[O-].[Cl-].[Y+3].[Cl-].[Cl-].[N+](=O)([O-])[O-].[Co+2].[N+](=O)([O-])[O-].[Cl-].[Y+3].[Cl-].[Cl-].C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+]>>C(C(=O)[O-])(=O)[O-].[Co+2].C(C(=O)[O-])(=O)[O-].[Y+3].C(C(=O)[O-])(=O)[O-].C(C(=O)[O-])(=O)[O-].[Y+3] | [O:1]=[C:2]([O-:3])[C:14](=[O:13])[O-:15].[Co+2:25].[Y+3:27]>>[O:1]=[C:2]([O-:3])[C:4](=[O:5])[O-:6].[O:7]=[C:8]([O-:9])[C:10](=[O:11])[O-:12].[O:13]=[C:14]([O-:15])[C:16](=[O:17])[O-:18].[Co+2:25].[Y+3:27] | O=C([O-])C(=O)[O-].[Co+2].[Y+3] | O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Co+2].[Y+3] | null | null | null | Acylation | OtherReaction | 03df169542e61bc25f850d05576488c0b54839b94e3082a72ebb3e4f24252841 | 46615a373e6434dd65776b88d9fcc22218d37124c5265a98f610d7564f54362b | null | [O;-;D1;H0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C;H0;D3;+0:4](-[O;-;D1;H0:5])=[O;D1;H0:6]>>[O;-;D1;H0:5]-[C;H0;D3;+0:4](=[O;D1;H0:6])-[C:7](-[O;-;D1;H0:8])=[O;D1;H0:9].[O;-;D1;H0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:10](-[O;-;D1;H0:11])=[O;D1;H0:12] | null | [] | 60 | CELSIUS | null | null | A solution of cobalt nitrate having a gravity of 1.30 g/cm3 was mixed homogeneously with a solution of yttrium chloride having a concentration of 67 g/l in a volume proportion of 520:1. The mixed solution was heated to 60° C. A solution of ammonium oxalate having a gravity of 1.06 g/cm3 and a pH 2.5 was added while sti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | null | 60 | null | O=C([O-])C(=O)[O-].[Co+2].[Y+3]>>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Co+2].[Y+3] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ba07d0f4cc294f878e1a0259559fe581 | O=C([O-])C(=O)[O-].[Ce+3]>>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Ce+3] | [N+](=O)([O-])[O-].[Ce+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[Ce+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+].C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+]>>C(C(=O)[O-])(=O)[O-].[Ce+3].C(C(=O)[O-])(=O)[O-].C(C(=O)[O-])(=O)[O-].[Ce+3] | [O:7]=[C:8]([O-:9])[C:10](=[O:11])[O-:12].[Ce+3:20]>>[O:7]=[C:8]([O-:9])[C:10](=[O:11])[O-:12].[O:13]=[C:14]([O-:15])[C:16](=[O:17])[O-:18].[Ce+3:20] | O=C([O-])C(=O)[O-].[Ce+3] | O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Ce+3] | null | [Co](Cl)Cl.[Co](Cl)Cl | null | Acylation | OtherReaction | 03df169542e61bc25f850d05576488c0b54839b94e3082a72ebb3e4f24252841 | 46615a373e6434dd65776b88d9fcc22218d37124c5265a98f610d7564f54362b | null | null | null | [] | 35 | CELSIUS | null | null | A solution of cobalt chloride having a gravity of 1.05 g/cm3 was mixed with a solution of cerium nitrate and heated to 35° C., followed by adding, while stirring a solution of ammonium oxalate having a gravity of 1.03 g/m3 and a pH 3. The quantity of ammonium oxalate added was 1.5 mole equivalent per mole equivalent of... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | [Co](Cl)Cl.[Co](Cl)Cl | 35 | null | O=C([O-])C(=O)[O-].[Ce+3]>[Co](Cl)Cl.[Co](Cl)Cl>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Ce+3] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-155ed44d0c004f6b88a366ddb1f96444 | O=C([O-])[O-]>>O=C([O-])[O-].O=C([O-])[O-].O=C([O-])[O-].[Nd+3] | [Cl-].[Nd+3].[Cl-].[Cl-].[Cl-].[NH4+].C([O-])([O-])=O.[Na+].[Na+]>>C([O-])([O-])=O.[Nd+3].C([O-])([O-])=O.C([O-])([O-])=O.[Nd+3] | [O:1]=[C:2]([O-:3])[O-:11]>>[O:1]=[C:2]([O-:3])[O-:4].[O:5]=[C:6]([O-:7])[O-:8].[O:9]=[C:10]([O-:11])[O-:12].[Nd+3:14] | O=C([O-])[O-] | O=C([O-])[O-].O=C([O-])[O-].O=C([O-])[O-].[Nd+3] | null | [Co](Cl)Cl | null | Functional Group Addition | OtherReaction | e206ff4710fef21b1959032f80be8ce6caf4b8538542903fc66ccfaa9095b638 | 69ece274e0104838fc859dee2bcf07ab566679ccfd515c3388e20b73f1d85347 | null | [O-;H0;D1:1]-[C;H0;D3;+0:2](-[O;-;D1;H0:3])=[O;D1;H0:4]>>[O-;H0;D1:1]-[C:5](-[O;-;D1;H0:6])=[O;D1;H0:7].[O;-;D1;H0:3]-[C;H0;D3;+0:2](-[O;-;D1;H0:8])=[O;D1;H0:4] | null | [] | 50 | CELSIUS | null | null | A solution of cobalt chloride having a gravity of 1.20 g/cm3 containing ammonium chloride was mixed while stirring with a solution of neodymium chloride and heated to 50° C. A stoichiometric equivalent quantity of sodium carbonate solution of 60° C. having a gravity of 1.05 g/cm3 was added to the mixed solution while s... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | [Co](Cl)Cl | 50 | null | O=C([O-])[O-]>[Co](Cl)Cl>O=C([O-])[O-].O=C([O-])[O-].O=C([O-])[O-].[Nd+3] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-042063d63f8a444cbb89063f7771e99d | O=C([O-])C(=O)[O-].[Sm+3]>>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Sm+3] | [N+](=O)([O-])[O-].[Sm+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].[Sm+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-].C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+].C(C(=O)[O-])(=O)[O-].[NH4+].[NH4+]>>C(C(=O)[O-])(=O)[O-].[Sm+3].C(C(=O)[O-])(=O)[O-].C(C(=O)[O-])(=O)[O-].[Sm+3] | [O:7]=[C:8]([O-:9])[C:10](=[O:11])[O-:12].[Sm+3:20]>>[O:7]=[C:8]([O-:9])[C:10](=[O:11])[O-:12].[O:13]=[C:14]([O-:15])[C:16](=[O:17])[O-:18].[Sm+3:20] | O=C([O-])C(=O)[O-].[Sm+3] | O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Sm+3] | null | [Co](Cl)Cl.[Co](Cl)Cl | null | Acylation | OtherReaction | 03df169542e61bc25f850d05576488c0b54839b94e3082a72ebb3e4f24252841 | 46615a373e6434dd65776b88d9fcc22218d37124c5265a98f610d7564f54362b | null | null | null | [] | 70 | CELSIUS | null | null | A solution of cobalt chloride having a gravity of 1.10 g/cm3 was mixed homogeneously with a solution of samarium nitrate having a concentration of 94 mg/ml in a volume proportion of 150:1. The mixed solution was heated to 70° C. A solution of ammonium oxalate having a gravity of 1.15 g/cm3 and a pH value of 5 was added... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | Other | [Co](Cl)Cl.[Co](Cl)Cl | 70 | null | O=C([O-])C(=O)[O-].[Sm+3]>[Co](Cl)Cl.[Co](Cl)Cl>O=C([O-])C(=O)[O-].O=C([O-])C(=O)[O-].[Sm+3] |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-0ee36df9d1a4484bb5c2bc1ce082fa65 | CC(=O)C=C(C)C.CC(=O)CCl.Oc1ccccc1>>CC(=Cc1ccc(O)cc1)c1ccc(O)cc1 | ClCC(C)=O.ClC(C(=O)C)Cl.O=C(C)C=C(C)C.C1(=CC=CC=C1)O.ClCC(C)=O.ClCC(C)=O.S(O)(O)(=O)=O>>OC1=CC=C(C=C1)C(=CC1=CC=C(C=C1)O)C | C[C:11](=[CH:12][C:13]([CH3:14])=[O:15])[CH3:17].O=[C:2]([CH3:1])[CH2:3]Cl.[cH:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]1 | CC(=O)C=C(C)C.CC(=O)CCl.Oc1ccccc1 | CC(=Cc1ccc(O)cc1)c1ccc(O)cc1 | null | null | C(Cl)Cl.O.CC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 4989ae325f9fc36c8d658ef523b9a488fca5867ad03ee9e9e5728e4d69cff7f2 | f622ea852e82bdf803a4d494081bd8b1fd55c59ed1b8c8399efa769463499ffb | C(=Cc1ccccc1)c1ccccc1 | C-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[CH;D2;+0:3]-[C;H0;D3;+0:4](-[CH3;D1;+0:5])=[O;H0;D1;+0:6].Cl-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=O)-[C;D1;H3:9].[c:10]:[c:11]:[cH;D2;+0:12]:[c:13]:[c:14]>>[C;D1;H3:9]-[C;H0;D3;+0:8](=[CH;D2;+0:7]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:11]:[c:10])-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D... | null | [] | -10 | CELSIUS | 16 | HOUR | Phenol (752.8 grams, 8.0 moles), chloroacetone (384.77 grams, 4.0 moles as chloroacetone) and methylene chloride (600 grams) are added to a reactor and cooled to -10° C. with stirring under a nitrogen atmosphere. The chloroacetone used is a commercial grade containing 96.25% chloroacetone, 0.05% acetone, 3.05% 1,1-dich... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone | Aromatic alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl.O.CC(=O)C | -10 | 16 | CC(=O)C=C(C)C.CC(=O)CCl.Oc1ccccc1>C(Cl)Cl.O.CC(=O)C>CC(=Cc1ccc(O)cc1)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-6ff4bdd1e3964baaae33d90c3af4eb2c | O=C(Cl)C(F)(F)C(F)(Br)C(F)(F)Br.Oc1c(I)cc(I)cc1I>>O=C(Oc1c(I)cc(I)cc1I)C(F)(F)C(F)(Br)C(F)(F)Br | C=1C(=CC(=C(C1I)O)I)I.FC(C(=O)Cl)(C(C(Br)(F)F)(Br)F)F>>IC1=C(C(=CC(=C1)I)I)OC(C(C(C(Br)(F)F)(Br)F)(F)F)=O | Cl[C:2](=[O:1])[C:13]([F:14])([F:15])[C:16]([F:17])([Br:18])[C:19]([F:20])([F:21])[Br:22].[OH:3][c:4]1[c:5]([I:6])[cH:7][c:8]([I:9])[cH:10][c:11]1[I:12]>>[O:1]=[C:2]([O:3][c:4]1[c:5]([I:6])[cH:7][c:8]([I:9])[cH:10][c:11]1[I:12])[C:13]([F:14])([F:15])[C:16]([F:17])([Br:18])[C:19]([F:20])([F:21])[Br:22] | O=C(Cl)C(F)(F)C(F)(Br)C(F)(F)Br.Oc1c(I)cc(I)cc1I | O=C(Oc1c(I)cc(I)cc1I)C(F)(F)C(F)(Br)C(F)(F)Br | null | null | N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[F;D1;H0:5])-[F;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 99 | [{"value": 99.0, "product": "IC1=C(C(=CC(=C1)I)I)OC(C(C(C(Br)(F)F)(Br)F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.2, "product": "IC1=C(C(=CC(=C1)I)I)OC(C(C(C(Br)(F)F)(Br)F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 100 grams of triiodophenol were dissolved in 100 ml of pyridine with warming to 50° C. 75 grams of 2,2,3,4,4-pentafluoro-3,4-dibromo-butyryl chloride were added dropwise through a dropping funnel with stirring at such a rate that the temperature did not rise above 65° C. The mixture was stirred at 50° C. for an additio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | 50 | null | O=C(Cl)C(F)(F)C(F)(Br)C(F)(F)Br.Oc1c(I)cc(I)cc1I>N1=CC=CC=C1>O=C(Oc1c(I)cc(I)cc1I)C(F)(F)C(F)(Br)C(F)(F)Br |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-af04e3fc60fd4e9a9acc5f15ce50eda6 | O=C(Cl)C(F)(F)C(F)(Br)C(F)(F)Br.Oc1c(I)cc(I)c(Br)c1I>>O=C(Oc1c(I)cc(I)c(Br)c1I)C(F)(F)C(F)(Br)C(F)(F)Br | BrC=1C(=C(C(=CC1I)I)O)I.FC(C(=O)Cl)(C(C(Br)(F)F)(Br)F)F>>IC1=C(C(=CC(=C1Br)I)I)OC(C(C(C(Br)(F)F)(Br)F)(F)F)=O | Cl[C:2](=[O:1])[C:14]([F:15])([F:16])[C:17]([F:18])([Br:19])[C:20]([F:21])([F:22])[Br:23].[OH:3][c:4]1[c:5]([I:6])[cH:7][c:8]([I:9])[c:10]([Br:11])[c:12]1[I:13]>>[O:1]=[C:2]([O:3][c:4]1[c:5]([I:6])[cH:7][c:8]([I:9])[c:10]([Br:11])[c:12]1[I:13])[C:14]([F:15])([F:16])[C:17]([F:18])([Br:19])[C:20]([F:21])([F:22])[Br:23] | O=C(Cl)C(F)(F)C(F)(Br)C(F)(F)Br.Oc1c(I)cc(I)c(Br)c1I | O=C(Oc1c(I)cc(I)c(Br)c1I)C(F)(F)C(F)(Br)C(F)(F)Br | null | null | N1=CC=CC=C1 | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[F;D1;H0:5])-[F;D1;H0:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | 20.3 grams of 3-bromo-2,4,6-triiodophenol (m.p 155°-157° C.) were dissolved in 50 ml of pyridine 13.0 grams of 2,2,3,4,4-pentafluoro-3,4-dibromo-butyryl chloride were added dropwise through a dropping funnel with stirring. The mixture was stirred overnight at room temperature. The mixture was washed in a separatory fun... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | null | null | O=C(Cl)C(F)(F)C(F)(Br)C(F)(F)Br.Oc1c(I)cc(I)c(Br)c1I>N1=CC=CC=C1>O=C(Oc1c(I)cc(I)c(Br)c1I)C(F)(F)C(F)(Br)C(F)(F)Br |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ee68d39c5e5542ca8e4b4663ce20dbb7 | CCC(C)COS(=O)(=O)c1ccc(C)cc1.Oc1ccc(O)cc1>>CCC(C)COc1ccc(O)cc1 | C1(=CC=C(C=C1)S(=O)(=O)OCC(CC)C)C.C1(O)=CC=C(O)C=C1.[OH-].[Na+]>>CC(COC1=CC=C(C=C1)O)CC | Cc1ccc(S(=O)(=O)O[CH2:5][CH:3]([CH2:2][CH3:1])[CH3:4])cc1.[OH:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1 | CCC(C)COS(=O)(=O)c1ccc(C)cc1.Oc1ccc(O)cc1 | CCC(C)COc1ccc(O)cc1 | null | null | O.C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4]):c:c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 72 | [{"value": 72.0, "product": "CC(COC1=CC=C(C=C1)O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.0, "product": "CC(COC1=CC=C(C=C1)O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 8 | HOUR | Into a n-butanol suspension containing 37 mmol (9.0 g) of 2-methylbutyl p-toluenesulfonate prepared by tosylating S-(-)-2-methylbutanol and 74 mmol (8.2 g) of hydroquinone, added dropwise was a solution of 50 mmol (2.1 g) of sodium hydroxide dissolved in a solvent mixture comprising 3 ml of water and 10 ml of n-butanol... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccccc1 | TsOH.HO- | O.C(CCC)O | 120 | 8 | CCC(C)COS(=O)(=O)c1ccc(C)cc1.Oc1ccc(O)cc1>O.C(CCC)O>CCC(C)COc1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4871f52327694f1cbe2e0f27dd59dbfe | CC[C@H](C)CO.O=C(O)c1ccc(O)cc1>>CCC(C)COC(=O)c1ccc(O)cc1 | OC1=CC=C(C(=O)O)C=C1.C[C@H](CO)CC.S(O)(O)(=O)=O.O>>OC1=CC=C(C(=O)OCC(CC)C)C=C1 | [CH3:1][CH2:2][C@H:3]([CH3:4])[CH2:5][OH:6].O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][O:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1 | CC[C@H](C)CO.O=C(O)c1ccc(O)cc1 | CCC(C)COC(=O)c1ccc(O)cc1 | null | null | C1(=CC=CC=C1)C | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "OC1=CC=C(C(=O)OCC(CC)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "OC1=CC=C(C(=O)OCC(CC)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.0 g of p-hydroxybenzoic acid and 12.5 g of (S)-(-)-2-methylbutanol were refluxed for 6 hours in toluene in the presence of sulfuric acid, while the generated water was removed out. Subsequently, the reaction solution was washed with water to remove sulfuric acid out. After the resulting solution was dried and concent... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC[C@H](C)CO.O=C(O)c1ccc(O)cc1>C1(=CC=CC=C1)C>CCC(C)COC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-4e95d25f5b2d41338d9ce44d7c9f9e29 | C=CCCCCCCBr.CCOC(=O)c1ccc(O)cc1>>C=CCCCCCCOc1ccc(C(=O)O)cc1 | [OH-].[Na+].BrCCCCCCC=C.OC1=CC=C(C(=O)OCC)C=C1.C([O-])([O-])=O.[K+].[K+].Cl>>C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1 | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].CC[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]([OH:9])[cH:18][cH:17]1)=[O:15]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1 | C=CCCCCCCBr.CCOC(=O)c1ccc(O)cc1 | C=CCCCCCCOc1ccc(C(=O)O)cc1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | 89 | [{"value": 89.0, "product": "C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | 9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Thereto added was an aqueous solution containing 2.4 g of sodium hydroxide, and then reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1 | HBr | C(C)O.O | null | 10 | C=CCCCCCCBr.CCOC(=O)c1ccc(O)cc1>C(C)O.O>C=CCCCCCCOc1ccc(C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-16d4578764164207b3fbaf490dfbb2e2 | C=CCCCCCCOc1ccc(C(=O)O)cc1.CCC(C)COC(=O)c1ccc(-c2ccc(O)cc2)cc1>>C=CCCCCCCOc1ccc(C(=O)OC2(C(=O)OCC(C)CC)C=CC(c3ccccc3)=CC2)cc1 | C1(=CC=CC=C1)C.OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OCC(CC)C.C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1>>C(CCCCCC=C)OC1=CC=C(C(=O)OC2(CC=C(C=C2)C2=CC=CC=C2)C(=O)OCC(CC)C)C=C1 | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:37][cH:38]1.O[c:32]1[cH:31][cH:30][c:29](-[c:28]2[cH:27][cH:26][c:17]([C:18](=[O:19])[O:20][CH2:21][CH:22]([CH3:23])[CH2:24][CH3:25])[cH:36][cH:35]2)[cH:34][cH:33]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH... | C=CCCCCCCOc1ccc(C(=O)O)cc1.CCC(C)COC(=O)c1ccc(-c2ccc(O)cc2)cc1 | C=CCCCCCCOc1ccc(C(=O)OC2(C(=O)OCC(C)CC)C=CC(c3ccccc3)=CC2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 5970bb0b8c5f14245f40354d421fb0187a208f7c579483617bc42fd7407d61e6 | cccdb3e2031a78ea1a4f6bbaca35c68350ada479b551e33135c361a7c1b1caca | O=C(OC1C=CC(c2ccccc2)=CC1)c1ccccc1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:2):[c:15]:[c:16]:1.[O;D1;H0:17]=[C:18](-[OH;D1;+0:19])-[c:20]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[C;H0;D4;+0:8]1(-[O;H0;D2;+0:19]-[C:18](=[O;D1;H0:17... | 45 | [{"value": 45.0, "product": "C(CCCCCC=C)OC1=CC=C(C(=O)OC2(CC=C(C=C2)C2=CC=CC=C2)C(=O)OCC(CC)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A toluene solution containing 10 g of 2-methylbutyl 4'-hydroxybiphenyl-4-carboxylate and 3 g of pyridine was added dropwise to the above-described toluene solution of the acid chloride compound. After conclusion of dropping, the temperature was raised, and reaction was carried out for 8 hours at 50° C. After conclusion... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Aromatic alcohol | Ester.Ester | c1ccccc1.c1ccccc1 | C1=CCCC=C1.c1ccccc1 | c1ccccc1.C1=CCCC=C1.c1ccccc1 | Other | N1=CC=CC=C1 | null | 8 | C=CCCCCCCOc1ccc(C(=O)O)cc1.CCC(C)COC(=O)c1ccc(-c2ccc(O)cc2)cc1>N1=CC=CC=C1>C=CCCCCCCOc1ccc(C(=O)OC2(C(=O)OCC(C)CC)C=CC(c3ccccc3)=CC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9ad13e2b1c894f9687888c893b7a5b06 | CC[C@H](C)CCO.O=C(O)c1ccc(O)cc1>>CCC(C)CCOC(=O)c1ccc(O)cc1 | OC1=CC=C(C(=O)O)C=C1.C[C@H](CCO)CC.S(O)(O)(=O)=O>>OC1=CC=C(C(=O)OCCC(CC)C)C=C1 | [CH3:1][CH2:2][C@H:3]([CH3:4])[CH2:5][CH2:6][OH:7].O[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][CH2:6][O:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][cH:16]1 | CC[C@H](C)CCO.O=C(O)c1ccc(O)cc1 | CCC(C)CCOC(=O)c1ccc(O)cc1 | null | null | C1(=CC=CC=C1)C | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 80.7 | [{"value": 80.0, "product": "OC1=CC=C(C(=O)OCCC(CC)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "OC1=CC=C(C(=O)OCCC(CC)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 13.7 g of p-hydroxybenzoic acid and 11.4 g of (S)-(+)-3-methyl-1-pentanol were refluxed for 10 hours in toluene in the presence of sulfuric acid, while removing out the generated water from the reaction system. Subsequently, the reaction solution was washed with water to remove the sulfuric acid out. The reaction solut... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC[C@H](C)CCO.O=C(O)c1ccc(O)cc1>C1(=CC=CC=C1)C>CCC(C)CCOC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b4a0964d88644cb69fc49099e36ac464 | CCC(C)CO.O=C(O)c1ccc(O)cc1>>CCC(C)COC(=O)c1ccc(O)cc1 | OC1=CC=C(C(=O)O)C=C1.CC(CO)CC.S(O)(O)(=O)=O>>OC1=CC=C(C(=O)OCC(CC)C)C=C1 | [CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][OH:6].O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][O:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1 | CCC(C)CO.O=C(O)c1ccc(O)cc1 | CCC(C)COC(=O)c1ccc(O)cc1 | null | null | C1(=CC=CC=C1)C | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 83 | [{"value": 83.0, "product": "OC1=CC=C(C(=O)OCC(CC)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "OC1=CC=C(C(=O)OCC(CC)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4.0 g of p-hydroxybenzoic acid and 12.5 g of (-)-2-methylbutanol were refluxed for 6 hours in toluene in the presence of sulfuric acid, while removing the generated water out from the reaction system. Subsequently, the reaction solution was washed with water to remove sulfuric acid out. The reaction solution was then d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCC(C)CO.O=C(O)c1ccc(O)cc1>C1(=CC=CC=C1)C>CCC(C)COC(=O)c1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-b4667a9cf3b446bd948f6814dceebf7a | CCC(C)COS(=O)(=O)c1ccc(C)cc1.Oc1ccc(O)cc1>>CCC(C)COc1ccc(O)cc1 | [OH-].[Na+].C1(=CC=C(C=C1)S(=O)(=O)OCC(CC)C)C.C1(O)=CC=C(O)C=C1>>CC(COC1=CC=C(C=C1)O)CC | Cc1ccc(S(=O)(=O)O[CH2:5][CH:3]([CH2:2][CH3:1])[CH3:4])cc1.[OH:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][CH:3]([CH3:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]1 | CCC(C)COS(=O)(=O)c1ccc(C)cc1.Oc1ccc(O)cc1 | CCC(C)COc1ccc(O)cc1 | null | null | O.C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | b5213736859cf91483a02f350869986d9b7674724716adef8a5d7a4bbdb79574 | 3d107e624e135e10014c7bf413dd0be27e1e4488f039e545b94cb1680b764158 | c1ccccc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C;D1;H3:4]):c:c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 72 | [{"value": 72.0, "product": "CC(COC1=CC=C(C=C1)O)CC", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 8 | HOUR | Into a n-butanol suspension containing 37 mmol (9.0 g) of 2-methylbutyl p-toluenesulfonate prepared by tosylating S-(-)-2-methylbutanol and 74 mmol (8.2 g) of hydroquinone, added dropwise was a solution of 50 mmol (2.1 g) of sodium hydroxide dissolved in a solvent mixture of 3 ml of water and 10 ml of n-butanol. After ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aromatic alcohol | Ether | c1ccccc1 | null | c1ccccc1 | TsOH.HO- | O.C(CCC)O | 120 | 8 | CCC(C)COS(=O)(=O)c1ccc(C)cc1.Oc1ccc(O)cc1>O.C(CCC)O>CCC(C)COc1ccc(O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-9b9269591a114f26bc8d123006fad2bc | CCCCCCC(F)COC(=O)c1ccc(O)cc1.c1ccncc1>>C=CCCCCCCCCOc1ccc(C(=O)Oc2ccc(C(=O)OCC(F)CCCCCC)cc2)cc1 | OC1=CC=C(C(=O)OCC(CCCCCC)F)C=C1.N1=CC=CC=C1>>C(CCCCCCCC=C)OC1=CC=C(C(=O)OC2=CC=C(C(=O)OCC(CCCCCC)F)C=C2)C=C1 | [OH:11][c:12]1[cH:20][cH:21][c:22]([C:23](=[O:17])[O:25][CH2:26][CH:27]([F:28])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[cH:35][cH:36]1.n1[cH:1][cH:15][cH:16][cH:38][cH:37]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][c:19]2[cH:... | CCCCCCC(F)COC(=O)c1ccc(O)cc1.c1ccncc1 | C=CCCCCCCCCOc1ccc(C(=O)Oc2ccc(C(=O)OCC(F)CCCCCC)cc2)cc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 3215c02c8917e25f623a8f514bc962444f4247eee63ac422ecd26cc0a85fb63c | 4b1a8ddd25f7286b891447ff4066a6be64fd5738c08b8ce175890008d0fe2ee6 | O=C(Oc1ccccc1)c1ccccc1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5]1:[c:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[OH;D1;+0:9]):[cH;D2;+0:10]:[c:11]:1.[cH;D2;+0:12]1:[cH;D2;+0:13]:[cH;D2;+0:14]:[cH;D2;+0:15]:n:[cH;D2;+0:16]:1>>[C:1]-[#8:2]-[C;H0;D3;+0:3](=[O;D1;H0:17])-[c:5]1:[c:6]:[cH;D2;+0:7]:[c:18](-[#8:19]-[C;H0;D3;+0:13](=[O;H0;D1;+0:4])-[c... | 167.8 | [{"value": 85.0, "product": "C(CCCCCCCC=C)OC1=CC=C(C(=O)OC2=CC=C(C(=O)OCC(CCCCCC)F)C=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 167.8, "product": "C(CCCCCCCC=C)OC1=CC=C(C(=O)OC2=CC=C(C(=O)OCC(CCCCCC)F)C=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To 3.0 g of 4-(9-decenyloxy)benzoic acid prepared in the same manner as in 9.(2) in Example 9 added was toluene, and the mixture was cooled in an ice bath. 2.0 g of thionyl chloride was added dropwise to the mixture. Subsequently, reaction was carried out for 3 hours at 80° C. After conclusion of the reaction, the prod... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol | Ester.Ester.Ether.Allyl | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | 15 | CCCCCCC(F)COC(=O)c1ccc(O)cc1.c1ccncc1>C1(=CC=CC=C1)C>C=CCCCCCCCCOc1ccc(C(=O)Oc2ccc(C(=O)OCC(F)CCCCCC)cc2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-ef446ce9b28342d0a62b3c6f5e5e4b49 | C=CCCCCCCBr.CCOC(=O)c1ccc(O)cc1>>C=CCCCCCCOc1ccc(C(=O)O)cc1 | [OH-].[Na+].BrCCCCCCC=C.OC1=CC=C(C(=O)OCC)C=C1.C([O-])([O-])=O.[K+].[K+].Cl>>C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1 | Br[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1].CC[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]([OH:9])[cH:18][cH:17]1)=[O:15]>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1 | C=CCCCCCCBr.CCOC(=O)c1ccc(O)cc1 | C=CCCCCCCOc1ccc(C(=O)O)cc1 | null | null | C(C)O.O | Heteroatom Alkylation and Arylation | OtherReaction | c47049bacd28cc701f2e77df376a2fcefecd5392e081f9a62473cff265d23a8c | 017337a0828c32d10d28543003ae15a8b492b5e2f69019c65a4461eabc617d95 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].C-C-[O;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11].[O;D1;H0:6]=[C:5](-[OH;D1;+0:4])-[c:7] | 89 | [{"value": 89.0, "product": "C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | 9.4 g of 8-bromo-1-octene, 9.0 g of ethyl p-hydroxybenzoate, and 7.6 g of potassium carbonate were refluxed in ethanol for 10 hours. Added thereto was an aqueous solution containing 2.4 g of sodium hydroxide, and reflux was further continued for 10 hours. After conclusion of the reaction, the reaction solution was dilu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | null | null | c1ccccc1 | HBr | C(C)O.O | null | 10 | C=CCCCCCCBr.CCOC(=O)c1ccc(O)cc1>C(C)O.O>C=CCCCCCCOc1ccc(C(=O)O)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-de7405e7ac6843299a46eac854633c2b | C=CCCCCCCOc1ccc(C(=O)O)cc1.CCC(C)COC(=O)c1ccc(-c2ccc(O)cc2)cc1>>C=CCCCCCCOc1ccc(C(=O)OC2(C(=O)OCC(C)CC)C=CC(c3ccccc3)=CC2)cc1 | C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1.C1(=CC=CC=C1)C.OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)OCC(CC)C.C1(=CC=CC=C1)C.C(CCCCCC=C)OC1=CC=C(C(=O)O)C=C1>>C(CCCCCC=C)OC1=CC=C(C(=O)OC2(CC=C(C=C2)C2=CC=CC=C2)C(=O)OCC(CC)C)C=C1 | [CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:37][cH:38]1.O[c:32]1[cH:31][cH:30][c:29](-[c:28]2[cH:27][cH:26][c:17]([C:18](=[O:19])[O:20][CH2:21][CH:22]([CH3:23])[CH2:24][CH3:25])[cH:36][cH:35]2)[cH:34][cH:33]1>>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH... | C=CCCCCCCOc1ccc(C(=O)O)cc1.CCC(C)COC(=O)c1ccc(-c2ccc(O)cc2)cc1 | C=CCCCCCCOc1ccc(C(=O)OC2(C(=O)OCC(C)CC)C=CC(c3ccccc3)=CC2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 5970bb0b8c5f14245f40354d421fb0187a208f7c579483617bc42fd7407d61e6 | cccdb3e2031a78ea1a4f6bbaca35c68350ada479b551e33135c361a7c1b1caca | O=C(OC1C=CC(c2ccccc2)=CC1)c1ccccc1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:2):[c:15]:[c:16]:1.[O;D1;H0:17]=[C:18](-[OH;D1;+0:19])-[c:20]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[C;H0;D4;+0:8]1(-[O;H0;D2;+0:19]-[C:18](=[O;D1;H0:17... | 45 | [{"value": 45.0, "product": "C(CCCCCC=C)OC1=CC=C(C(=O)OC2(CC=C(C=C2)C2=CC=CC=C2)C(=O)OCC(CC)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 9 g of p-(7-octenyloxy)benzoic acid obtained in 15.(1) was suspended in toluene, and the suspension was cooled in an ice bath. Added dropwise thereto was 6 g of thionyl chloride. After conclusion of the dropping, the temperature was raised and reaction was carried out for 6 hours at 80° C. After conclusion of the react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Aromatic alcohol | Ester.Ester | c1ccccc1.c1ccccc1 | C1=CCCC=C1.c1ccccc1 | c1ccccc1.C1=CCCC=C1.c1ccccc1 | Other | N1=CC=CC=C1 | null | 8 | C=CCCCCCCOc1ccc(C(=O)O)cc1.CCC(C)COC(=O)c1ccc(-c2ccc(O)cc2)cc1>N1=CC=CC=C1>C=CCCCCCCOc1ccc(C(=O)OC2(C(=O)OCC(C)CC)C=CC(c3ccccc3)=CC2)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-91bea4c5979044409b42d000b2acefe8 | C=CCCCCCCCCOc1ccc(C(=O)O)cc1.O=S(Cl)Cl>>CCCCCCCCC=COc1ccc(C(=O)Cl)cc1 | C(CCCCCCCC=C)OC1=CC=C(C(=O)O)C=C1.S(=O)(Cl)Cl>>C(=CCCCCCCCC)OC1=CC=C(C(=O)Cl)C=C1 | O[C:16]([c:15]1[cH:14][cH:13][c:12]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=[CH2:1])[cH:20][cH:19]1)=[O:17].O=S(Cl)[Cl:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][O:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[Cl:18])[cH:19][cH:20]1 | C=CCCCCCCCCOc1ccc(C(=O)O)cc1.O=S(Cl)Cl | CCCCCCCCC=COc1ccc(C(=O)Cl)cc1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | f22d8c06beac88659adbb692e51cc5543127556f28cdc88fd1e77f11fd400ed0 | ade055367122c9e6e7b5cc537acd4e6f43d157ea0fa12ab2d6126061495606e0 | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[#8:11]-[c:12].[C:13]-[C:14]-[CH;D2;+0:15]=[CH2;D1;+0:16]>>[C:13]-[C:14]-[CH2;D2;+0:15]-[CH3;D1;+0:16].[C:7]-[C:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-[#8:11]-[c:12].[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[... | null | [] | null | null | 7 | HOUR | To 2.8 g of p-(9-decenyloxy)benzoic acid prepared in the same manner as in 9.(2) in Example 9 added was toluene, and the resulting mixture was cooled in an ice bath. 5.0 g of thionyl chloride was then added dropwise to the toluene solution. Reaction was then carried out for 7 hours at 80° C. After conclusion of the rea... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Allyl | Acyl halide.Ether | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 7 | C=CCCCCCCCCOc1ccc(C(=O)O)cc1.O=S(Cl)Cl>C1(=CC=CC=C1)C>CCCCCCCCC=COc1ccc(C(=O)Cl)cc1 |
ord_dataset-02ee2261663048188cf6d85d2cc96e3f | ord-a595f883ebd94deb981e91be38be3c2a | Nc1nc(N)nc(N)n1>>Nc1nc(N)nc(N)n1 | N1=C(N)N=C(N)N=C1N.C=O.[OH-].[Na+]>>C=O.N1=C(N)N=C(N)N=C1N | [NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1>>[NH2:3][c:4]1[n:5][c:6]([NH2:7])[n:8][c:9]([NH2:10])[n:11]1 | Nc1nc(N)nc(N)n1 | Nc1nc(N)nc(N)n1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ncncn1 | null | null | [] | 60 | CELSIUS | null | null | Separately, a mixture comprising 10 parts of melamine, 25 parts of 37% aqueous formaldehyde solution and 65 parts of water was adjusted to pH 9.0 with sodium hydroxide and was heated at 60° C. with stirring to perform dissolution to obtain a transparent melamine-formaldehyde precondensate.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ncncn1 | null | O | 60 | null | Nc1nc(N)nc(N)n1>O>Nc1nc(N)nc(N)n1 |
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