(1S)-2-amino-1-phenylethan-1-ol → (2S,4EZ)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino)-1-[(2-methyl[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide

HRID 1349345Notes

Reaction equation

HRID 1349345 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[CH3:19][C:20]1[CH:25]=[C:24](C(O)=O)[CH:23]=[CH:22][C:21]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH2:35][CH2:36][C@H:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[OH:38]>>[OH:38][C@@H:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:36][NH:35][C:16]([C@@H:9]1[CH2:10][C:11](=[N:13][O:14][CH3:15])[CH2:12][N:8]1[C:6]([C:24]1[CH:23]=[CH:22][C:21]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:20]([CH3:19])[CH:25]=1)=[O:7])=[O:18]

Participants

4

Reactant 3

HCID 643217(1S)-2-amino-1-phenylethan-1-olHCID 215218102-Methyl-[1,1'-biphenyl]-4-carboxylic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726423(2S,4EZ)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino)-1-[(2-methyl[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 2-methyl[1,1′-biphenyl]-4-carboxylic acid, and (1S)-2-amino-1-phenylethanol, the title compound was obtained in 95% purity by HPLC. MS(ESI+): m/z=472.

Sources & evidence

ORD record
ord-64693c85a8ff44e0973ac8a3bd514bae
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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