Hydrochloric Acid → (4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-thienyl)-4-thiazolidinecarboxylic acid

HRID 223706Notes

Reaction equation

HRID 223706 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7]1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:21][CH2:22][C:23](Cl)=[O:24].[C:26]([O-:34])(=[S:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[K+].Cl>O>[C:26]([S:33][CH2:21][CH2:22][C:23]([N:10]1[C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7][CH:6]1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:24])(=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 6710826(R)-2-Thiophen-2-ylthiazolidine-4-carboxylic acidHCID 23681850Potassium thiobenzoate

Product 1

HCID 12915812(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-thienyl)-4-thiazolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.8 g of (4R)-2-(2-thienyl)-4-thiazolidinecarboxylic acid and 10.6 g of sodium carbonate are dissolved in 100 ml of water and 8.6 g of 3-bromopropanoyl chloride is added dropwise while stirring under ice-cooling. After the addition, the mixture is stirred under ice-cooling for 2 hours. To this reaction solution, 8.8 g of potassium thiobenzoate is added and stirred at room temperature for 1 hour. The solution is acidified with dilute hydrochloric acid and 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 in vacuo to give the titled compound, yield 11.6 g (57%), mp. 141°-143° C. (benzene), [α]D25 +107.7° (c=1.0, methanol).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. temperaturecooling for 2 hours
  5. stirringstirred at room temperature for 1 hour
  6. extractionthe produced oil is extracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f90d061f8ab94a4db7b18efc0aee0b83
Source dataset
uspto-grants-1982_10
Patent number
US04356183

Reaction notes

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