Benzyl Alcohol → 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid benzylester
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22](=[O:32])[NH:23][CH2:24][CH:25]([CH3:31])[CH2:26][C:27]([F:30])([F:29])[F:28])[CH:20]=2)[NH:15][CH:14]=1)[C:6]([OH:8])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:52](O)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:52]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22](=[O:32])[NH:23][CH2:24][CH:25]([CH3:31])[CH2:26][C:27]([F:28])([F:29])[F:30])[CH:20]=3)[NH:15][CH:14]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid (1.54 grams, 3.43 mmol), triphenylphosphine (1.26 grams, 4.8 mmol) and benzyl alcohol (0.50 mL, 4.8 mmol) in tetrahydrofuran (50 mL), at 0° C., was added diethyl azodicarboxylate (0.65 mL, 4.1 mmol). The reaction is then warmed to room temperature and stirred 12 hours. Concentration in vacuo followed by chromatography on silica gel (1:1 hexanes:ethyl acetate) gave 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid benzylester with impurities present. The product was dissolved in cold ether, and filtered. The filtrate was concentrated, and the remaining yellow foam was chromatographed on silica gel (1:1 cyclohexane:ethyl acetate) to give 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid benzylester (1.56 grams, 87% yield).
Workup
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-a3721e8762b441c9ae2bf58babf2b98c
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05965745
Reaction notes
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