Methanol → HCID 66676905, compound

HRID 423279Notes

Reaction equation

C[O:2][C:3](=[O:38])[CH2:4][NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])=[C:10]([C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[CH:9]=1.CO.[OH-].[Na+]>C1COCC1>[CH3:36][N:34]([CH3:35])[C:33]([C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[NH:14][C:15]([C:17]1[C:18]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:32])[F:31])=[CH:27][CH:28]=2)=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:16])[CH2:7][CH2:6][NH:5][CH2:4][C:3]([OH:38])=[O:2])=[O:37]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixed solution of ({3-dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]benzyl}methylamino)acetic acid methyl ester (120 mg) in THF (1 mL)-methanol (3 mL) was added 4N aqueous sodium hydroxide (0.2 mL) The mixture was stirred at 50° C. for 2 hours under heating, allowed to stand for cooling down to room temperature, and concentrated in vacuo. After addition of water to the residue, 1N hydrochloric acid was added portionwise to the aqueous solution under ice-cooling to adjust the pH to 6 to 7, followed by extraction with ethyl acetate four times. The extract was dried over anhydrous sodium sulfate and concentrated to give the title compound (110 mg).

Workup

temperatureunder heating
temperaturefor cooling down to room temperature
concentrationconcentrated in vacuo
additionAfter addition of water to the residue, 1N hydrochloric acid
additionwas added portionwise to the aqueous solution under ice-
temperaturecooling
extractionfollowed by extraction with ethyl acetate four times
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-c040999c413940a0b7358fa67a418b80
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101774B2

Reaction notes

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