Sodium → HCID 11740974, compound

HRID 231826Notes

Reaction equation

HRID 231826 reaction equation
CO[CH:3](C1C=CC=CC=1)[CH2:4][O:5][C:6]([C:8]1[CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:10]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])=[C:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7].[Na]>C(O)C>[CH:19]([O:18][C:16]([C:10]1[CH:9]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:8]([C:6]([O:5][CH2:4][CH3:3])=[O:7])=[C:13]([CH3:14])[NH:12][C:11]=1[CH3:15])=[O:17])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 67923843HCID 67923843, compound2×

Product 1

HCID 11740974HCID 11740974, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

19 g (38 mmols) of (+)-1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-carboxylic acid isopropyl 2-methoxy-2-phenylethyl ester (compound A) in a solution of 0.87 g (38 mmols) of sodium in 100 ml of ethanol are heated to the boiling point under nitrogen for 8 hours. The solvent is then distilled off in vacuo, the residue is taken up in water and the mixture is acidified with dilute hydrochloric acid and extracted several times with methylene chloride. The extracts are concentrated in vacuo, after drying over sodium sulphate. The residue crystallised completely and is filtered off and recrystallised from methanol (crude yield: 4.1 g (2,%), melting point: 143°-146° C.), and the product is purified by high performance liquid chromatography, as described under

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. extractionextracted several times with methylene chloride
  3. concentrationThe extracts are concentrated in vacuo
  4. dry with materialafter drying over sodium sulphate
  5. customThe residue crystallised completely
  6. filtrationis filtered off
  7. customrecrystallised from methanol (crude yield: 4.1 g (2,%), melting point: 143°-146° C.)
  8. customthe product is purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-b4e9331ef8db47f9aac49d06adc69fb1
Source dataset
uspto-grants-1989_07
Patent number
US04849433

Reaction notes

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