Benzoyl chloride → (2S,4EZ)-1-benzoyl-4-benzylidene-N-(9-ethyl-9H-carbazol-3-yl)-2-pyrrolidinecarboxamide

HRID 1745181Notes

Reaction equation

HRID 1745181 reaction equation
[CH:1](=[C:8]1[CH2:12][N:11]([C:13]([O:15]C(C)(C)C)=O)[C@H:10]([C:20]([OH:22])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH2:32]([N:34]1[C:46]2[CH:45]=[CH:44][C:43]([NH2:47])=[CH:42][C:41]=2[C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH3:33]>>[C:13]([N:11]1[CH2:12][C:8](=[CH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@H:10]1[C:20]([NH:47][C:43]1[CH:44]=[CH:45][C:46]2[N:34]([CH2:32][CH3:33])[C:35]3[C:40]([C:41]=2[CH:42]=1)=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:22])(=[O:15])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 85883-Amino-9-ethylcarbazoleHCID 69250545(2S,4EZ)-4benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69250412(2S,4EZ)-1-benzoyl-4-benzylidene-N-(9-ethyl-9H-carbazol-3-yl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-benzylidene-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, benzoyl chloride, and 9-ethyl-9H-carbazol-3-amine the title compound was obtained in 81% purity by LC/MS. MS(ESI+): m/z=500.4.

Sources & evidence

ORD record
ord-b0c25114dce6479abbbe64086306fb78
Source dataset
uspto-grants-2006_03
Patent number
US07018988B2

Reaction notes

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