1-(2-Hydroxyethyl)piperazine → (3EZ5S)-1-[(3',4'-dichloro[1,1'-biphenyl]-4-yl)carbonyl]-5-{[4(2-hydroxyethyl)-1-piperazinyl]carbonyl}-3-pyrrolidinone O-methyloxime

HRID 1349331Notes

Reaction equation

HRID 1349331 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.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:32]=[CH:31][C:30](C(O)=O)=[CH:29][CH:28]=2)[CH:23]=[CH:24][C:25]=1[Cl:26].[N:36]1([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>>[CH3:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:16]([N:39]2[CH2:40][CH2:41][N:36]([CH2:42][CH2:43][OH:44])[CH2:37][CH2:38]2)=[O:18])[N:8]([C:6]([C:30]2[CH:29]=[CH:28][C:27]([C:22]3[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=3)=[CH:32][CH:31]=2)=[O:7])[CH2:12]1

Participants

4

Reactant 3

HCID 76771-(2-Hydroxyethyl)piperazineHCID 27581564-(3,4-Dichlorophenyl)benzoic acidHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726418(3EZ5S)-1-[(3',4'-dichloro[1,1'-biphenyl]-4-yl)carbonyl]-5-{[4(2-hydroxyethyl)-1-piperazinyl]carbonyl}-3-pyrrolidinone O-methyloxime

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 3′,4′-dichloro[1,1′-biphenyl]-4carboxylic acid, and 2-(1-piperazinyl)ethanol, the title compound was obtained in 86% purity by HPLC. MS(ESI+): m/z =520.

Sources & evidence

ORD record
ord-876d00e00b3146b186865f19973a2c5d
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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