Ethanol → HCID 23004146, compound

HRID 396673Notes

Reaction equation

HRID 396673 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6](=[O:23])[C:7](=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:8](=O)[CH2:9][CH2:10]C)#[N:2].[NH2:24][C:25]([CH2:37][CH3:38])=[CH:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].[CH3:39]CO>>[CH2:30]([O:29][C:27]([C:26]1[CH:13]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)[C:7]([C:6]([O:5][CH2:4][CH2:3][C:1]#[N:2])=[O:23])=[C:8]([CH2:9][CH3:10])[NH:24][C:25]=1[CH2:37][CH2:38][CH3:39])=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 54056370HCID 54056370, compoundHCID 70029593HCID 70029593, compound

Product 1

HCID 23004146HCID 23004146, compound

Procedure

A solution of 2-[(4-nitrophenyl)methylene]-3-oxohexanoic acid 2-cyanoethyl ester (16.3 g, 50 mmol) and benzyl 3-amino-2-pentenoate (11.3 g, 55 mmol) in 250 ml of EtOH was refluxed for 36 hrs. After the solvent was removed in vacuo, the residue was dissolved in 250 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 3-benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-6-ethyl-1,4-dihydro-4-(4-nitrophenyl)-2-propylpyridine was obtained as a yellow oil (25.1 g, 98%).

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 250 ml of CHCl3
  3. washwashed with water (2×100 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of solvent

Sources & evidence

ORD record
ord-5af31b38cd1e402ca8cea2f75544bf2f
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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