Methanol → 2-[2-methyl-3-[4-[4-(trifluoromethyl)benzamido]benzyl]-1H-indol-1-yl]acetic acid

HRID 589342Notes

Reaction equation

HRID 589342 reaction equation
[CH3:1][C:2]1[N:3]([CH2:31][C:32]([O:34]CC)=[O:33])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.O.[OH-].[Li+].O1CCCC1.CO>O>[CH3:1][C:2]1[N:3]([CH2:31][C:32]([OH:34])=[O:33])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:30])[C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89590294ethyl 2-[2-methyl-3-[4-[4-(trifluoromethyl)benzamido]benzyl]-1H-indol-1-yl]acetate

Product 1

HCID 715717102-[2-methyl-3-[4-[4-(trifluoromethyl)benzamido]benzyl]-1H-indol-1-yl]acetic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dry reaction vessel, ethyl 2-[2-methyl-3-[4-[4-(trifluoromethyl)benzamido]benzyl]-1H-indol-1-yl]acetate (600 mg, 1.21 mmol), lithium hydroxide monohydrate (153 mg, 3.64 mmol), 10 mL tetrahydrofuran, 10 mL methanol, 10 mL water were weighed, and stirred at room temperature for 1 h. The reaction was monitored to be complete by TLC. The solvent was rotate evaporated. It was adjusted to pH=3-4 with 2 N HCl solution. It was filtered, and the filter cake was washed with 20 mL methanol to obtain the product 480 mg as a white solid, at a yield of 85.1%.

Workup

  1. customThe solvent was rotate evaporated
  2. filtrationIt was filtered
  3. washthe filter cake was washed with 20 mL methanol

Sources & evidence

ORD record
ord-66c8ed0cbd844bf5885023b30e8a7b6b
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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