Citric Acid → HCID 9907804, compound

HRID 2297725Notes

Reaction equation

HRID 2297725 reaction equation
C([S:4][CH2:5][CH2:6][N:7]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:8](=[O:21])[NH:9][C@@H:10]([CH3:20])[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])(=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[SH:4][CH2:5][CH2:6][N:7]([CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:8](=[O:21])[NH:9][C@@H:10]([CH3:20])[C:11]([N:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86586959HCID 86586959, compound

Product 1

HCID 9907804HCID 9907804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(2S)-2-[3-[2-(Acetylthio)ethyl]-3-phenethylureido]propionyl]-4-methylpiperazine (Compound No. 13-2, 36.6 g) is dissolved in methanol (87 ml) under a nitrogen atmosphere, and the solution is cooled with ice. A 1 N aqueous sodium hydroxide solution (87 ml) is added dropwise thereto, and the mixture is stirred under ice cooling for 10 minutes. A 10% aqueous citric acid solution is added to the reaction mixture under ice cooling to adjust pH to 7. The mixture is concentrated under reduced pressure, a10% aqueous sodium hydrogencarbonate solution (300 ml) is added to the concentrate, and the whole is extracted with ethyl acetate. The organic layer is washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give the titled compound (Compound No. 30-1).

Workup

  1. temperaturethe solution is cooled with ice
  2. concentrationThe mixture is concentrated under reduced pressure
  3. additiona10% aqueous sodium hydrogencarbonate solution (300 ml) is added to the concentrate
  4. extractionthe whole is extracted with ethyl acetate
  5. washThe organic layer is washed with water and saturated brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14448280734d43759c64018c567e14cc
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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