Benzene → 3-Methyl 5-(1-methylethyl) 4-(4-benzofurazanyl)-1,2,3,4-tetrahydro-2-hydroxy-6-methyl-2-phenyl-3,5-pyridinedicarboxylate

HRID 364957Notes

Reaction equation

HRID 364957 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]=O)=[CH:7][CH:8]=[CH:9][C:2]=12.[O:12]=[C:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:14][C:15]([O:17][CH3:18])=[O:16].[NH:25]1CCCCC1.[C:31]([OH:38])(=[O:37])[CH2:32][CH2:33][CH2:34]CC.[CH:39]1[CH:44]=CC=C[CH:40]=1>C(OCC)(=O)C>[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:32]([C:31]([O:38][CH:39]([CH3:44])[CH3:40])=[O:37])=[C:33]([CH3:34])[NH:25][C:13]([OH:12])([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:14]3[C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

7

Reactant 5

HCID 241BenzeneHCID 8082PiperidineHCID 8892Hexanoic AcidHCID 348462Methyl 3-oxo-3-phenylpropanoateHCID 102908732,1,3-Benzoxadiazole-4-carbaldehyde

Product 1

HCID 700905073-Methyl 5-(1-methylethyl) 4-(4-benzofurazanyl)-1,2,3,4-tetrahydro-2-hydroxy-6-methyl-2-phenyl-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Benzofurazancarboxaldehyde (2.96 g, 20 mmoles), methyl beta-oxobenzenepropanoate (3.56 g, 20 mmoles), piperidine (0.05 ml) and hexanoic acid (0.13 ml) were heated at reflux for 3 hours in benzene (50 ml) using a Dean and Stark apparatus. The reaction was cooled, diluted with ethyl acetate and washed in turn with water, brine and saturated sodium bicarbonate and dried (Na2SO4). The solvent was removed in vacuo and the residue dissolved in ethanol (6 ml). 1-Methylethyl 3-amino-2-butenoate (3.0 g) and diethylamine (0.6 ml) were added and the mixture heated at 60° for 34 hours. The reaction mixture was cooled, evaporated to dryness in vacuo and the residue was dissolved in 2-propanol and treated with charcoal. The charcoal was filtered off and the title compound (1.1 g) was obtained on addition of cyclohexane mp 132°-4°.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed in turn with water, brine and saturated sodium bicarbonate
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in ethanol (6 ml)
  6. addition1-Methylethyl 3-amino-2-butenoate (3.0 g) and diethylamine (0.6 ml) were added
  7. temperaturethe mixture heated at 60° for 34 hours
  8. temperatureThe reaction mixture was cooled
  9. customevaporated to dryness in vacuo
  10. dissolutionthe residue was dissolved in 2-propanol
  11. additiontreated with charcoal
  12. filtrationThe charcoal was filtered off

Sources & evidence

ORD record
ord-f7321abefe1045eea948a0a69b9c1577
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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