Water → HCID 57683247, compound

HRID 1864952Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (51 mg) was dissolved in dimethylformamide (5 mL), and the solution was cooled to 0° C. To the solution was added the 4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenylacetic acid ethyl ester (500 mg) obtained in Example 1e), and the mixture was stirred for one hour. After addition of iodomethane (183 mg), the mixture was stirred at room temperature for 3 hours and water was then added. The reaction solution was concentrated, diluted with ethyl acetate, and washed with water. The resulting solution was dried over sodium sulfate and purified by column chromatography on silica gel with hexane:ethyl acetate=4:1 to give the title compound (141 mg).

Workup

stirringthe mixture was stirred at room temperature for 3 hours
concentrationThe reaction solution was concentrated
additiondiluted with ethyl acetate
washwashed with water
dry with materialThe resulting solution was dried over sodium sulfate
custompurified by column chromatography on silica gel with hexane

Sources & evidence

ORD record: ord-fe2b2e5b7fa648eaacfc455a3869db2e
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625948B2

Reaction notes

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