4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acid → HCID 58717981, compound

HRID 1245131Notes

Reaction equation

HRID 1245131 reaction equation
C[O:2][C:3](=[O:8])[C@@H:4]([NH2:7])[CH2:5][NH2:6].[F:9][C:10]([F:27])([F:26])[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>>[F:26][C:10]([F:9])([F:27])[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([NH:7][C@@H:4]([CH2:5][NH:6][C:23]([C:20]3[CH:19]=[CH:18][C:17]([C:14]4[CH:15]=[CH:16][C:11]([C:10]([F:9])([F:26])[F:27])=[CH:12][CH:13]=4)=[CH:22][CH:21]=3)=[O:24])[C:3]([OH:2])=[O:8])=[O:24])=[CH:21][CH:22]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 27827194'-(Trifluoromethyl)-[1,1'-biphenyl]-4-carboxylic acidHCID 10975468HCID 10975468, compound

Product 1

HCID 58717981HCID 58717981, compoundYield 60%

Procedure

(2S)-2,3-Diamino-propionic acid methyl ester (0.080 g, 0.421 mmol) was reacted with 4′-trifluoromethyl-biphenyl-4-carboxylic acid (0.224 g, 0.841 mmol) as described in general procedure A yielding the corresponding (2S)-3-bis-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid methyl ester which was then hydrolyzed as per general procedure C to yield the title compound (0.150 g, 60%). 1H-NMR(400 MHz, DMSOd6): 4.16 (m, 2H), 5.0 (m, 1H), 8.17 (m, 8H), 8.28 (m, 8H), 9.18 (m, 1H), 9.21 (d, 1H); LC/MS (m/z): 601.2 (M+1).

Sources & evidence

ORD record
ord-b38071531f1e43f891bb4ac85cd47c53
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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