1-(3,4-Dichlorophenyl)piperazine → (3EZ,5S)-5-{[4-(3 4-dichlorophenyl)-1-piperazinyl]carbonyl}-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-3-pyrrolidinone O-benzyloxime

HRID 1349049Notes

Reaction equation

HRID 1349049 reaction equation
[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15]([O:17]C(C)(C)C)=O)[C@H:12]([C:22]([OH:24])=O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:25]=[C:26]1[C:31](C(Cl)=O)=[CH:30][CH:29]=[C:28]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[O:27]1.[Cl:40][C:41]1[CH:42]=[C:43]([N:48]2[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]2)[CH:44]=[CH:45][C:46]=1[Cl:47]>>[CH2:1]([O:8][N:9]=[C:10]1[CH2:11][C@@H:12]([C:22]([N:51]2[CH2:50][CH2:49][N:48]([C:43]3[CH:44]=[CH:45][C:46]([Cl:47])=[C:41]([Cl:40])[CH:42]=3)[CH2:53][CH2:52]2)=[O:24])[N:13]([C:15]([C:31]2[C:26](=[O:25])[O:27][C:28]([CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:29][CH:30]=2)=[O:17])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 936011-(3,4-Dichlorophenyl)piperazineHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 131725420(2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726369(3EZ,5S)-5-{[4-(3 4-dichlorophenyl)-1-piperazinyl]carbonyl}-1-[(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl]-3-pyrrolidinone O-benzyloxime

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 1-(3,4-dichlorophenyl)piperazine the title compound was obtained in 47% purity by LC/MS. MS(ESI+): m/z=639.8.

Sources & evidence

ORD record
ord-2c45a507a5a04e2fa762badf48a6d69d
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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