(1,1'-Biphenyl)-4-sulphonyl chloride → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylsulfonyl)-N-[(2RS)-2-hydroxy-2-(2 naphthyl)ethyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1745261Notes

Reaction equation

HRID 1745261 reaction equation
C(OC([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)(C)(C)C.[C:19]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.[NH2:35][CH2:36][CH:37]([C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)[OH:38]>>[C:19]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:24]=[CH:23][C:22]([S:25]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]2[C:16]([NH:35][CH2:36][CH:37]([OH:38])[C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=2)=[O:18])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 27353792-Amino-1-(naphthalen-2-yl)ethan-1-olHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725591(2S,4EZ)-1-([1,1'-biphenyl]-4-ylsulfonyl)-N-[(2RS)-2-hydroxy-2-(2 naphthyl)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-sulfonyl chloride, and (1RS)-2-amino-1-(2-naphthyl)ethanol, the title compound was obtained in 77% purity by HPLC. MS(ESI+): m/z=544.

Sources & evidence

ORD record
ord-fa34645f3d6140b19fa500c0d4d9ec73
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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