4-Phenylbenzoyl chloride → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N-[(2S)-2-hydroxy-2-phenyl-ethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1745294Notes

Reaction equation

HRID 1745294 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.[C:19]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22](C(Cl)=O)=[CH:21][CH:20]=1.[NH2:34][CH2:35][C@H:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[OH:37]>>[C:28]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:29]=[CH:30][C:31]([C:6]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]2[C:16]([NH:34][CH2:35][C@@H:36]([OH:37])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:18])=[O:7])=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 643217(1S)-2-amino-1-phenylethan-1-olHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725623(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N-[(2S)-2-hydroxy-2-phenyl-ethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, [1,1′-biphenyl]-4-carbonyl chloride, and (1S)-2-amino-1-phenylethanol, the title compound was obtained in 87% purity by HPLC. MS(ESI+): m/z=458.

Sources & evidence

ORD record
ord-9477a70bce864c5a8b0582dbc80254d3
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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