(S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-aminopropanoate → 3-Biphenyl-4-yl-(2S)-[(7-bromo-isoquinoline-3-carbonyl)-amino]-propionic Acid

HRID 1245059Notes

Reaction equation

HRID 1245059 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[CH:30]=[C:29]2[C:24]([CH:25]=[C:26]([C:31](O)=[O:32])[N:27]=[CH:28]2)=[CH:23][CH:22]=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:31]([C:26]2[N:27]=[CH:28][C:29]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[C:21]([Br:20])[CH:30]=3)=[O:32])[C:3]([OH:2])=[O:19])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 15714801(S)-Methyl 3-([1,1'-biphenyl]-4-yl)-2-aminopropanoateHCID 219214267-Bromoisoquinoline-3-carboxylic acid

Product 1

HCID 587175343-Biphenyl-4-yl-(2S)-[(7-bromo-isoquinoline-3-carbonyl)-amino]-propionic AcidYield 81%

Procedure

(2S)-amino-3-biphenyl-4yl-propionic acid methyl ester (340 mg, 13.9 mmol) was reacted with 7-bromo-isoquinoline-3-carboxylic acid (350 mg, 13.9 mmol) as described in general procedure A. The resulting compound was hydrolyzed by following general procedure C yielding the title compound (132 mg, 81%) as a white solid.

Sources & evidence

ORD record
ord-df615ce932de4adeaa72e423034d4e63
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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