Ethyl Acetate → 3-Acetylsulfanyl-2-benzylsulfanylmethyl-propionic acid

HRID 1830132Notes

Reaction equation

HRID 1830132 reaction equation
[CH2:1]([S:8][CH2:9][C:10](=[CH2:14])[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:15]1C=CC=C1CC(O)=O.[C:24]([O:27]CC)(=O)[CH3:25]>C(Cl)Cl>[C:24]([S:15][CH2:14][CH:10]([CH2:9][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]([OH:13])=[O:12])(=[O:27])[CH3:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159702-Thiopheneacetic acidHCID 220539822-Benzylsulfanylmethylacrylic acid

Product 1

HCID 220539433-Acetylsulfanyl-2-benzylsulfanylmethyl-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-benzylsulfanylmethyl-acrylic acid (0.208 g) in methylene chloride (2.5 mL) was treated with thiolacetic acid and stirred at room temperature for 72 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and then washed twice with water and once with saturated aqueous sodium chloride. After drying over magnesium sulfate the solvent was removed by rotary evaporation and the residue chromatographed on silica gel eluting with an ethyl acetate/hexane/acetic acid mixture to produce 3-acetylsulfanyl-2-benzylsulfanylmethyl-propionic acid (0.208 g).

Workup

  1. washwashed twice with water and once with saturated aqueous sodium chloride
  2. dry with materialAfter drying over magnesium sulfate the solvent
  3. customwas removed by rotary evaporation
  4. customthe residue chromatographed on silica gel eluting with an ethyl acetate/hexane/acetic acid mixture

Sources & evidence

ORD record
ord-27ae98e210b54e0fb6b042a1f33fc162
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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