Methanol → 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid
Reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:30])[NH:21][CH2:22][CH:23]([CH3:29])[CH2:24][C:25]([F:28])([F:27])[F:26])[CH:18]=3)[NH:13][CH:12]=2)=[C:6]([O:31][CH3:32])[CH:5]=1.CO.O1CCCC1.O.[OH-].[Li+]>O>[CH3:32][O:31][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:30])[NH:21][CH2:22][CH:23]([CH3:29])[CH2:24][C:25]([F:26])([F:27])[F:28])[CH:18]=2)[NH:13][CH:12]=1)[C:3]([OH:33])=[O:2]Participants
6
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 methylester (1.80 grams, 3.90 mmol) in 2:2:1 methanol:tetrahydrofuran:water (30 mL) was added lithium hydroxide monohydrate (0.82 grams, 19.50 mmol). The resulting solution was stirred, at room temperature, for 48 hours then concentrated in vacuo. The resulting crude product was treated with 1 M hydrochloric acid (aq), and the resulting precipitate was collected via filtration to vie 3-methoxy-4-[5-(4,4,4-trifluoro-2-methyl-butylcarbamoyl)-1H-indol-3-ylmethyl]-benzoic acid (1.74 grams, 99% yield).
Workup
- concentrationthen concentrated in vacuo
- additionThe resulting crude product was treated with 1 M hydrochloric acid (aq)
- filtrationthe resulting precipitate was collected via filtration
Sources & evidence
- ORD record
- ord-5c6f55c5416245228c4a77b25a6ac0cb
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05965745
Reaction notes
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