Hydrochloric Acid → (4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(4-methylphenyl)-4-thiazolidinecarboxylic acid

HRID 1388123Notes

Reaction equation

HRID 1388123 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[NH:12][C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:22]([S:30][CH2:31][C@H:32]([CH3:36])[C:33](Cl)=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O>[C:22]([S:30][CH2:31][C@@H:32]([CH3:36])[C:33]([N:12]1[C@H:11]([C:13]([OH:15])=[O:14])[CH2:10][S:9][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2825743(4R)-2-(4-methylphenyl)-1,3-thiazolidine-4-carboxylic acidHCID 12878434(2S)-3-benzoylthio-2-methylpropionyl chloride

Product 1

HCID 12915626(4R)-3-[(2S)-S-Benzoyl-3-mercapto-2-methylpropanoyl]-2-(4-methylphenyl)-4-thiazolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.5 g of (4R)-2-(4-methylphenyl)-4-thiazolidinecarboxylic acid and 4.3 g of sodium carbonate are dissolved in 25 ml of water and 4.9 g of (2S)-S-benzoyl-3-mercapto-2-methylpropanoyl chloride is added dropwise while stirring under ice-cooling. After the addition, the mixture is stirred under ice-cooling for 1 hour and acidified with dilute hydrochloric acid. The produced oil is extracted with ethyl acetate. The ethyl acetate layer is washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to dryness in vacuo to give oil. The produced oil is purified by silica gel column chromatography to give the titled compound, yield 4.0 g (48%), mp. 131°-132° C. (ethyl acetatehexane), [α]D26 +117.6° (c=1.0, methanol).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. temperaturecooling for 1 hour
  5. extractionThe produced oil is extracted with ethyl acetate
  6. washThe ethyl acetate layer is washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customto give oil
  10. customThe produced oil is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6e93ef06c7ff4083b9f606f425e0e75d
Source dataset
uspto-grants-1984_02
Patent number
US04430344

Reaction notes

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