1-(2-Hydroxyethyl)piperazine → 4'-{[(2S,4EZ)-2-{[4-(2-hydroxyethyl)-1-piperazinyl]carbonyl}-4-(methoxyimino)pyrrolidinyl]carbonyl}[1,1'-biphenyl]-2-carbonitrile

HRID 1745334Notes

Reaction equation

HRID 1745334 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].[N:36]1([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[OH:44][CH2:43][CH2:42][N:36]1[CH2:41][CH2:40][N:39]([C:16]([C@@H:9]2[CH2:10][C:11](=[N:13][O:14][CH3:15])[CH2:12][N:8]2[C:6]([C:30]2[CH:29]=[CH:28][C:27]([C:22]3[C:21]([C:19]#[N:20])=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:32][CH:31]=2)=[O:7])=[O:18])[CH2:38][CH2:37]1

Participants

4

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 107277894-(2-cyanophenyl)benzoic AcidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 1317256624'-{[(2S,4EZ)-2-{[4-(2-hydroxyethyl)-1-piperazinyl]carbonyl}-4-(methoxyimino)pyrrolidinyl]carbonyl}[1,1'-biphenyl]-2-carbonitrile

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 2-(1-piperazinyl)ethanol, the title compound was obtained in 89% purity by HPLC. MS(ESI+): m/z=476.

Sources & evidence

ORD record
ord-abefecc838054a5a9df0d803b1b8ab24
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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