Methyl 3-aminocrotonate → 2-(4-Azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine

HRID 382752Notes

Reaction equation

HRID 382752 reaction equation
[C:1]([CH2:3][CH2:4][O:5][C:6](=[O:27])[C:7](=[CH:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:8](=O)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]=[N+:14]=[N-:15])#[N:2].[NH2:28]/[C:29](/[CH3:35])=[CH:30]\[C:31]([O:33][CH3:34])=[O:32]>CCO>[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][C:8]1[NH:28][C:29]([CH3:35])=[C:30]([C:31]([O:33][CH3:34])=[O:32])[CH:17]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[C:7]=1[C:6]([O:5][CH2:4][CH2:3][C:1]#[N:2])=[O:27])=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 643918Methyl 3-aminocrotonateHCID 538699817-Azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester

Product 1

HCID 865866352-(4-Azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl ester (2.87 g, 7.73 mmol) and methyl 3-aminocrotonate (0.900 g, 7.73 mmol) in 50 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=95:5). 2-(4-Azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (2.43 g, 67% yield).

Workup

  1. customAfter the EtOH was removed in vacuo
  2. dissolutionthe residue was dissolved in 150 ml of CHCl3
  3. washwashed with water (2×100 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of solvent
  6. customthe product was purified by chromatography (SiO2, CHCl3:MeOH=95:5)

Sources & evidence

ORD record
ord-dadd9eac384744c3878609f877286d2e
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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