Peracetic Acid → HCID 20189413, compound

HRID 1789024Notes

Reaction equation

HRID 1789024 reaction equation
C(OO)(=[O:3])C.[CH3:6][C:7]1[NH:8][C:9]([S:32][CH3:33])=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:6][C:7]1[NH:8][C:9]([S:32]([CH3:33])=[O:3])=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 516892Sodium BicarbonateHCID 20189407HCID 20189407, compound

Product 1

HCID 20189413HCID 20189413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Peracetic acid (6.8 ml of 1M solution in methanol) was added to a solution of diethyl 1,4-dihydro-2-methyl-6-(methylthio)-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (2.77 g 6.8 mmoles) in methylene chloride (150 ml) at -78°. The reaction mixture was allowed to reach room temperature and was then stirred for 30 minutes. Saturated aqueous sodium bicarbonate (150 ml) was added and the organic layer separated, dried (Na2SO4) and the solvent removed in vacuo. The residue was chromatographed on silica, eluting with ether/petroleum ether (60°-80° ) mixtures. The two isomers were separated and recrystallised from 2-propanol.

Workup

  1. customto reach room temperature
  2. customthe organic layer separated
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was chromatographed on silica
  6. washeluting with ether/petroleum ether (60°-80° )
  7. customThe two isomers were separated
  8. customrecrystallised from 2-propanol

Sources & evidence

ORD record
ord-b069d5e6788f4a148d76392c428235c7
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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