Benzo-1,3-dioxole-5-methylamine → (2S,4EZ)-N-(1,3-benzodioxol-5-ylmethyl)-4-[(benzyloxy)imino]-1-(4-cyanobenzoyl)-2-pyrrolidinecarboxamide

HRID 1349059Notes

Reaction equation

HRID 1349059 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.[C:25]([C:27]1[CH:35]=[CH:34][C:30](C(Cl)=O)=[CH:29][CH:28]=1)#[N:26].[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([CH2:45][NH2:46])=[CH:44][C:39]=2[O:38][CH2:37]1>>[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([CH2:45][NH:46][C:22]([C@@H:12]3[CH2:11][C:10](=[N:9][O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:14][N:13]3[C:15](=[O:17])[C:30]3[CH:29]=[CH:28][C:27]([C:25]#[N:26])=[CH:35][CH:34]=3)=[O:24])=[CH:44][C:39]=2[O:38][CH2:37]1

Participants

4

Reactant 3

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 801724-Cyanobenzoyl chlorideHCID 131725420(2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131726370(2S,4EZ)-N-(1,3-benzodioxol-5-ylmethyl)-4-[(benzyloxy)imino]-1-(4-cyanobenzoyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(benzyl-oxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 4-cyanobenzoyl chloride, and 1,3-benzodioxol-5-ylmethylamine the title compound was obtained in 51% purity by LC/MS. MS(ESI+): m/z=497.6.

Sources & evidence

ORD record
ord-0ab7e0409ad9436f97c45561dac7f986
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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