Triethylamine → (4R)-3-[(2S)-S-Benzoyl-3-mercapto-2methylpropanoyl]-2-(2-thienyl)-4-thiazolidinecarboxylic acid

HRID 1462002Notes

Reaction equation

HRID 1462002 reaction equation
[C:1]([S:9][CH2:10][C@@H:11]([CH3:15])[C:12]([OH:14])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[S:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH:36]1[NH:40][C@H:39]([C:41]([OH:43])=[O:42])[CH2:38][S:37]1>O1CCCC1.O>[C:1]([S:9][CH2:10][C@@H:11]([CH3:15])[C:12]([N:40]1[C@H:39]([C:41]([OH:43])=[O:42])[CH2:38][S:37][CH:36]1[C:32]1[S:31][CH:35]=[CH:34][CH:33]=1)=[O:14])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 6710826(R)-2-Thiophen-2-ylthiazolidine-4-carboxylic acidHCID 12763916(S)-3-(benzoylthio)-2-methylpropionic acid

Product 1

HCID 12915816(4R)-3-[(2S)-S-Benzoyl-3-mercapto-2methylpropanoyl]-2-(2-thienyl)-4-thiazolidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

11.2 g of (2S)-S-benzoyl-3-mercapto-2-methylpropanoic acid and 5.1 g of triethylamine are dissolved in 100 ml of dehydrated tetrahydrofuran. To this solution, 6.8 g of isobutyl chloroformate is added dropwise while stirring at the temperature maintained -5° C. After the addition, the mixture is stirred at room temperature for 10 minutes. To this solution, 10.8 g of (4R)-2-(2-thienyl)-4-thiazolidinecarboxylic acid and 5.1 g of triethylamine dissolved in the mixed solution of 5 ml of tetrahydrofuran and 15 ml of water are added. The mixture is stirred at room temperature for 30 minutes. To this reaction mixture, 200 ml of water is added and the mixture is extracted with ethyl acetate. The aqueous layer is acidified with dilute hydrochloric acid and the produced oil is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the titled compound, yield 10.3 g (49%), mp. 136°-137° C. (benzene), [α]D25 +79.6° (c=1.0, methanol).

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred at room temperature for 10 minutes
  3. additionare added
  4. stirringThe mixture is stirred at room temperature for 30 minutes
  5. extractionthe mixture is extracted with ethyl acetate
  6. extractionthe produced oil is extracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de5b5e2c7774476c9b9765e37a8e7671
Source dataset
uspto-grants-1984_07
Patent number
US04457935

Reaction notes

Loading…