Sodium Thiosulfate → (S)-2-acetylthio-3-phenylpropanoic acid

HRID 10928

Reaction equation

HRID 10928 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Cl[C@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[C:1]([S:3][C@@H:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 11458104(2R)-chloro-3-phenylpropionic acidHCID 23670855Potassium ethanethioate

Product 1

HCID 10176891(S)-2-acetylthio-3-phenylpropanoic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium thioacetate (68 mg, 0.64 mmol) was added to a solution of 100 mg (0.54 mmol) of the (2R)-2-chloro-3-phenylpropionic acid obtained in Example 14 in 2 ml of dimethylformamide at room temperature, and the mixture was stirred for 24 hours. A 6% aqueous solution of sodium thiosulfate (0.5 ml) was added to the reaction mixture, and the whole mixture was extracted with 30 ml of ethyl acetate. The organic phase was washed with 3 ml of 6% sodium thiosulfate aqueous solution, 3 ml of water and 3 ml of a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. The solvent was removed under reduced pressure to give 101 mg (yield 83%) of the desired (2S)-2-acetylthio-3-phenylpropionic acid.

Workup

  1. extractionthe whole mixture was extracted with 30 ml of ethyl acetate
  2. washThe organic phase was washed with 3 ml of 6% sodium thiosulfate aqueous solution, 3 ml of water and 3 ml of a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-908bddf74474441f8443475f190a40a2
Source dataset
uspto-grants-2006_08
Patent number
US07094926B2

Linked notes

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