4-Phenylbenzoyl chloride → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N-[(3R)-3-hydroxy-3-phenyl-propyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1745342Notes

Reaction equation

HRID 1745342 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][CH2:36][C@H:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[OH:38]>>[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][CH2:36][C@@H:37]([OH:38])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:18])=[O:7])=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 11182697(R)-3-Amino-1-phenyl-propan-1-olHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725669(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N-[(3R)-3-hydroxy-3-phenyl-propyl]-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]4carbonyl chloride, and (1R)-3-amino-1-phenyl-1-propanol, the title compound was obtained in 94% purity by HPLC. MS(ESI+): m/z=472.

Sources & evidence

ORD record
ord-91af094a23df47f9a6fa3b8465f40923
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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