trans-(2-Aminocyclohexyl)methanol → (2S,4EZ)-1-[(2'-cyano[1,1'-biphenyl]-4-yl)carbonyl]-N-[(1R,2R)-2-(hydroxymethyl)cyclohexyl]-4-(methoxyimino)-2-pyrrolidinecarboxamide

HRID 1349321Notes

Reaction equation

HRID 1349321 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]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30](C(O)=O)=[CH:29][CH:28]=1)#[N:20].[NH2:36][C@@H:37]1[CH2:42][CH2:41][CH2:40][CH2:39][C@H:38]1[CH2:43][OH:44]>>[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[CH:29][C:30]([C:6]([N:8]2[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]2[C:16]([NH:36][C@@H:37]2[CH2:42][CH2:41][CH2:40][CH2:39][C@H:38]2[CH2:43][OH:44])=[O:18])=[O:7])=[CH:31][CH:32]=1)#[N:20]

Participants

4

Reactant 3

HCID 2724655trans-(2-Aminocyclohexyl)methanolHCID 107277894-(2-cyanophenyl)benzoic AcidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726414(2S,4EZ)-1-[(2'-cyano[1,1'-biphenyl]-4-yl)carbonyl]-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, 2′-cyano[1,1′-biphenyl]-4-carboxylic acid, and [(1R,2R)-2-aminocyclohexyl]methanol, the title compound was obtained in 78% purity by HPLC. MS(ESI+): m/z=475.

Sources & evidence

ORD record
ord-d6ed0404a5504d36bf34e3bb99402315
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

Loading…