Trimethylamine → 3-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}propionic acid ethyl ester

HRID 423271Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14](=[O:18])[N:15]([CH3:17])[CH3:16])[CH:8]=1)[CH3:2].CN(C)C.[F:24][C:25]([F:42])([F:41])[C:26]1[CH:31]=[CH:30][C:29]([C:32]2[C:33]([C:38](Cl)=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:28][CH:27]=1>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:38]([C:33]2[C:32]([C:29]3[CH:30]=[CH:31][C:26]([C:25]([F:24])([F:41])[F:42])=[CH:27][CH:28]=3)=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:39])=[C:9]([C:14](=[O:18])[N:15]([CH3:16])[CH3:17])[CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-Amino-3-dimethylcarbamoylphenyl)propionic acid ethyl ester (1.52 g) was dissolved in ethyl acetate (10 mL), and trimethylamine (533 mg) was added thereto. After cooling down to 0° C., 4′-trifluoromethylbiphenyl-2-carbonyl chloride (synthesized from the corresponding carboxylic acid 0.529 g) was added thereto, and the mixture was stirred at room temperature overnight. After filtration of the insoluble material, the filtrate was concentrated and purified by column chromatography on silica gel (ethyl acetate:hexane=3:2, v/v) to give the title compound (0.843 g).

Workup

additionwas added
filtrationAfter filtration of the insoluble material
concentrationthe filtrate was concentrated
custompurified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record: ord-f8c63a0f87ab4de8b4e1b78ed2642a8f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101774B2

Reaction notes

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