(Z)-Benzyl 3-aminobut-2-enoate → 3-Benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine

HRID 322176Notes

Reaction equation

HRID 322176 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6](=[O:21])[C:7](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[C:8](=O)[CH3:9])#[N:2].[NH2:22]/[C:23](/[CH3:35])=[CH:24]\[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>CCO>[CH2:28]([O:27][C:25]([C:24]1[CH:11]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:7]([C:6]([O:5][CH2:4][CH2:3][C:1]#[N:2])=[O:21])=[C:8]([CH3:9])[NH:22][C:23]=1[CH3:35])=[O:26])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 5368345(Z)-Benzyl 3-aminobut-2-enoateHCID 543622242-((4-Nitrophenyl)methylene]-3-oxobutanoic acid 2-cyanoethyl ester

Product 1

HCID 107188283-Benzyloxycarbonyl-5-(2-cyanoethoxy)carbonyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[(4-nitrophenyl)methylene]-3-oxobutanoic acid 2-cyanoethyl ester (15.06 g, 52.3 mmol) and benzyl 3-amino-crotonate (10.00 g, 52.3 mmol) in 150 ml of EtOH was refluxed for 36 hrs. After solvent was evaporated, 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-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine was obtained as a yellow oil (23.4 g, 97%).

Workup

  1. customAfter solvent was evaporated
  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-4ef46c1d71224c798f5b55ce85062ccd
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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