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

HRID 964277Notes

Reaction equation

HRID 964277 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-fe11c69f7191457883a131786f582202
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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