Sodium Hydroxide → 4-(3-Chlorophenyl)-2,6-dimethyl-5-(methyl-(3-phenyl-2-propene-1-yl)carbamoyl)-1,4-dihydropyridine-3-carboxylic acid

HRID 1700340Notes

Reaction equation

HRID 1700340 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14](=[O:26])[N:15]([CH3:25])[CH2:16][CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([CH3:27])[NH:11][C:10]([CH3:28])=[C:9]2[C:29]([O:31]CCC#N)=[O:30])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].S([O-])(O)(=O)=O.[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14](=[O:26])[N:15]([CH3:25])[CH2:16][CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:12]([CH3:27])[NH:11][C:10]([CH3:28])=[C:9]2[C:29]([OH:31])=[O:30])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 701564182-Cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(methyl-(3-phenyl-2-propene-1-yl)carbamoyl)-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 701577374-(3-Chlorophenyl)-2,6-dimethyl-5-(methyl-(3-phenyl-2-propene-1-yl)carbamoyl)-1,4-dihydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

224 mg (0.456 mmol) of 2-cyanoethyl 4-(3-chlorophenyl)-2,6-dimethyl-5-(methyl-(3-phenyl-2-propene-1-yl)carbamoyl)-1,4-dihydropyridine-3-carboxylate was dissolved in 4.6 ml of methanol. 0.456 ml of 1 N aqueous sodium hydroxide solution was added to the obtained solution, and they were stirred at room temperature overnight. An aqueous potassium hydrogensulfate solution was added to the reaction mixture. Methanol was evaporated under reduced pressure. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1) to obtain the title compound.

Workup

  1. customMethanol was evaporated under reduced pressure
  2. extractionAfter the extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-6e0e97174fc048dd8ea4f7535b3d4708
Source dataset
uspto-grants-2002_02
Patent number
US06350762B1

Reaction notes

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