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

HRID 589352Notes

Reaction equation

HRID 589352 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([C:6]([NH:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]([O:26]CC)=[O:25])[C:15]=3[CH3:29])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.O.[OH-].[Li+].O1CCCC1.CO>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:31]=[CH:30][C:12]([CH2:13][C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][C:24]([OH:26])=[O:25])[C:15]=3[CH3:29])=[CH:11][CH:10]=2)=[O:7])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 90449096ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetate

Product 1

HCID 715717132-[3-[4-(4-chlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetic acidYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dry reaction vessel, ethyl 2-[3-[4-(4-chlorobenzamido)benzyl]-2-methyl-1H-indol-1-yl]acetate (580 mg, 1.26 mmol), lithium hydroxide monohydrate (159 mg, 3.79 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 as a white solid 523 mg, at a yield of 95.9%.

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-144ca34f7610447fa7fc6727cf997337
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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