Benzoyl chloride → (3EZ,5S)-5-{[4-(1,3-benzodioxol-5-ylmethyl)-1-piperazinyl]carbonyl]-1-benzoyl-3-pyrrolidinone O-(3,4-dichlorobenzyl)oxime

HRID 1349046Notes

Reaction equation

HRID 1349046 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=O)=[O:7])(C)(C)C.C(Cl)(=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([CH2:45][N:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)=[CH:44][C:39]=2[O:38][CH2:37]1>>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[Cl:22])[CH2:15][O:14][N:13]=[C:11]1[CH2:10][C@@H:9]([C:24]([N:49]2[CH2:48][CH2:47][N:46]([CH2:45][C:43]3[CH:42]=[CH:41][C:40]4[O:36][CH2:37][O:38][C:39]=4[CH:44]=3)[CH2:51][CH2:50]2)=[O:26])[N:8]([C:6](=[O:7])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:12]1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 944261-PiperonylpiperazineHCID 131725417(2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725429(3EZ,5S)-5-{[4-(1,3-benzodioxol-5-ylmethyl)-1-piperazinyl]carbonyl]-1-benzoyl-3-pyrrolidinone O-(3,4-dichlorobenzyl)oxime

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-{[(3,4-dichlorobenzyl)oxy]imino}-2-pyrrolidinecarboxylic acid, benzoyl chloride, and 1-(1,3-benzodioxol-5-ylmethyl)piperazine the title compound was obtained in 71% purity by LC/MS. MS(ESI+): m/z=609.8.

Sources & evidence

ORD record
ord-e7772e52efd3411e84613d55c5a09854
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

Loading…