(1,1'-Biphenyl)-4-sulphonyl chloride → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylsulfonyl)-N-[(1R,2R)-2-(hydroxymethyl)-cyclohexyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1745289Notes

Reaction equation

HRID 1745289 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][C@@H:36]1[CH2:41][CH2:40][CH2:39][CH2:38][C@H:37]1[CH2:42][OH:43]>>[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][C@@H:36]2[CH2:41][CH2:40][CH2:39][CH2:38][C@H:37]2[CH2:42][OH:43])=[O:18])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 2724655trans-(2-Aminocyclohexyl)methanolHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725618(2S,4EZ)-1-([1,1'-biphenyl]-4-ylsulfonyl)-N-[(1R,2R)-2-(hydroxymethyl)-cyclohexyl]-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]-4sulfonyl chloride, and [(1R,2R)-2-aminocyclohexyl]methanol, the title compound was obtained in 40% purity by HPLC. MS(ESI+): m/z=486.

Sources & evidence

ORD record
ord-cd79db85bc9d4f7fbae09dc47eed50d5
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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