Veratrylamine → (2S,4EZ)-4-(cyanomethylene)-N-(3,4-dimethoxybenzyl)-1-(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl-2-pyrrolidinecarboxamide

HRID 1349099Notes

Reaction equation

HRID 1349099 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[CH:13][C:14]#[N:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[O:19]=[C:20]1[C:25](C(Cl)=O)=[CH:24][CH:23]=[C:22]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:21]1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][C:43]=1[O:44][CH3:45])[CH2:39][NH2:40]>>[C:14]([CH:13]=[C:11]1[CH2:12][N:8]([C:6]([C:25]2[C:20](=[O:19])[O:21][C:22]([CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:23][CH:24]=2)=[O:7])[C@H:9]([C:16]([NH:40][CH2:39][C:38]2[CH:41]=[CH:42][C:43]([O:44][CH3:45])=[C:36]([O:35][CH3:34])[CH:37]=2)=[O:18])[CH2:10]1)#[N:15]

Participants

4

Reactant 3

HCID 79832VeratrylamineHCID 222235122-oxo-6-pentyl-2H-pyran-3-carbonyl chlorideHCID 69250314(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid

Product 1

HCID 69250614(2S,4EZ)-4-(cyanomethylene)-N-(3,4-dimethoxybenzyl)-1-(2-oxo-6-pentyl-2H-pyran-3-yl)carbonyl-2-pyrrolidinecarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(cyanomethylene)-2-pyrrolidinecarboxylic acid, 2-oxo-6-pentyl-2H-pyran-3-carbonyl chloride, and 3,4-dimethoxybenzylamine the title compound was obtained in 65% purity by LC/MS. MS(ESI+): m/z=494.4.

Sources & evidence

ORD record
ord-df49a3464aac4f47af6be5ef5bdf7bf6
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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