Potassium Carbonate → (S)-2-acetylthio-3-phenylpropanoic acid

HRID 2392950

Reaction equation

HRID 2392950 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14]>O.[OH-].[Na+]>[C:1]([S:3][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11746403(R)-2-Bromo-3-phenylpropionic acidHCID 178418634HCID 178418634, compound

Product 1

HCID 10176891(S)-2-acetylthio-3-phenylpropanoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Thioacetic acid (9.3 cc) and potassium carbonate (7.5 g) in water (150 cc) are added under nitrogen atmosphere to a solution of (R)-2-bromo-3-phenylpropanoic acid (25 g) in 1M sodium hydroxide (110 cc). The solution is stirred for 15 hours at a temperature close to 20° C. After evaporation under reduced pressure, the residue is taken up with water and ethyl acetate. The aqueous phase is separated, acidified to pH=2 and then extracted with ethyl acetate. After washing, the organic phase is dried over sodium sulphate. After filtration and concentration under reduced pressure, (S)-2-acetylthio-3-phenylpropanoic acid (18.5 g) is obtained with a yield of 75% in the form of an oil having the following characteristics: Rf =0.49 [hexane/ethyl acetate/acetic acid (6:4:0.5 by volume)].

Workup

  1. customclose to 20° C
  2. customAfter evaporation under reduced pressure
  3. customThe aqueous phase is separated
  4. extractionextracted with ethyl acetate
  5. washAfter washing
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-c9c58ca911f949558a745ede45b469b5
Source dataset
uspto-grants-1998_09
Patent number
US05801274

Linked notes

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