Furfurylamine → (2S,4EZ)-4-[(benzyloxy)imino]-1-(4-cyanobenzoyl)-N-(2-furylmethyl)-2-pyrrolidinecarboxamide

HRID 1349035Notes

Reaction equation

HRID 1349035 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[CH:40]=[CH:39][CH:38]=[C:37]1[CH2:41][NH2:42]>>[CH2:1]([O:8][N:9]=[C:10]1[CH2:14][N:13]([C:15](=[O:17])[C:30]2[CH:29]=[CH:28][C:27]([C:25]#[N:26])=[CH:35][CH:34]=2)[C@H:12]([C:22]([NH:42][CH2:41][C:37]2[O:36][CH:40]=[CH:39][CH:38]=2)=[O:24])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 3438FurfurylamineHCID 801724-Cyanobenzoyl chlorideHCID 131725420(2S,4EZ)-4[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725419(2S,4EZ)-4-[(benzyloxy)imino]-1-(4-cyanobenzoyl)-N-(2-furylmethyl)-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-4-[(benzyloxy)imino]-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid, 4-cyanobenzoyl chloride, and 2-furylmethylamine the title compound was obtained in 49% purity by LC/MS. MS(ESI+): m/z=443.4.

Sources & evidence

ORD record
ord-12774c425c48480da08e7b6aae4358f4
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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