3-Bromo-5-chloro-2,6-dimethoxybenzoic acid → 3-Biphenyl-4-yl-2-(S)-(3-bromo-5-chloro-2,6-dimethoxy-benzoylamino)-propionic acid

HRID 2373846

Reaction equation

HRID 2373846 reaction equation
C[O:2][C:3](=[O:19])[C@@H:4]([NH2:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Br:20][C:21]1[C:22]([O:33][CH3:34])=[C:23]([C:27]([O:31][CH3:32])=[C:28]([Cl:30])[CH:29]=1)[C:24](O)=[O:25]>>[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:11][C:6]([CH2:5][C@H:4]([NH:18][C:24](=[O:25])[C:23]2[C:27]([O:31][CH3:32])=[C:28]([Cl:30])[CH:29]=[C:21]([Br:20])[C:22]=2[O:33][CH3:34])[C:3]([OH:2])=[O:19])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 28004633-Bromo-5-chloro-2,6-dimethoxybenzoic acidHCID 15714801(S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-aminopropanoate

Product 1

HCID 112145373-Biphenyl-4-yl-2-(S)-(3-bromo-5-chloro-2,6-dimethoxy-benzoylamino)-propionic acidYield 80.6%

Procedure

2-(S)-amino-3-biphenyl-4-yl-propionic acid methyl ester (128 mg, 0.5 mmol) was reacted with 3-bromo-5-chloro-2,6-dimethoxybenzoic acid (148 mg, 0.5 mmol) as described in general procedure A. The resulting compound was hydrolyzed according to general procedure C to afford the title product (209 mg) as a pure white solid.

Sources & evidence

ORD record
ord-89c162e8b9094729a4a59f739fd14519
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Linked notes

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