4-(Trifluoromethyl)phenylboronic acid → 3-Biphenyl-4-yl-2-(S)-[(5-chloro-2,4-dimethoxy-4'-trifluoromethyl-biphenyl-3-carbonyl)-amino]-propionic acid

HRID 2373845

Reaktionsgleichung

Reaktionsgleichung von HRID 2373845
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[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]([OH:26])=O.[F:35][C:36]([F:47])([F:46])[C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1>>[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]([C:23]2[C:22]([O:33][CH3:34])=[C:21]([C:40]3[CH:41]=[CH:42][C:37]([C:36]([F:47])([F:46])[F:35])=[CH:38][CH:39]=3)[CH:29]=[C:28]([Cl:30])[C:27]=2[O:31][CH3:32])=[O:26])[C:3]([OH:2])=[O:19])=[CH:7][CH:8]=1

Komponenten

4

Edukt 3

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 28004633-Bromo-5-chloro-2,6-dimethoxybenzoic acidHCID 15714801(S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-aminopropanoate

Produkt 1

HCID 598526103-Biphenyl-4-yl-2-(S)-[(5-chloro-2,4-dimethoxy-4'-trifluoromethyl-biphenyl-3-carbonyl)-amino]-propionic acidAusbeute 61,6 %

Versuchsvorschrift

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 crude compound was reacted with 195 mg (1.0 mmol) of 4-(trifluoromethyl)phenylboronic acid as described in general procedure D. The product thus obtained was hydrolyzed according to general procedure C to afford the title product (180 mg) as a pure white solid.

Aufarbeitung

  1. customThe product thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-57a1e2897391479c81088f07a62eddf8
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07459472B2

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