2-[(Acetylthio)methyl]-phenylpropionic acid

Chemical Properties

Brownish Liquid

Uses

2-[(Acetylthio)methyl]-phenylpropionic acid is a racecadotril intermediate. It is also a β-thiopropionyl-amino acid derivative used as β-lactamase inhibitor.

Synthesis

General procedure for the synthesis of 3-(acetylthio)-2-benzylpropionic acid from 2-benzylpropenoic acid and thioacetic acid: 16.2 g of 2-benzylpropenoic acid and 12.3 mL of thioacetic acid were added to a clean and dry round-bottomed flask, and the reaction was stirred for 1 hour at 30 °C. Subsequently, the reaction mixture was warmed up to 60 °C and the stirring reaction was continued for 4 hours. Upon completion of the reaction, the excess thioacetic acid was removed by distillation to give the crude product of 3-(acetylthio)-2-benzylpropionic acid. Yield: 23.8 g.

References

[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 15, p. 2461 - 2476
[2] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3389 - 3393
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 20, p. 5614 - 5619
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 3, p. 602 - 608
[5] Magnetic Resonance in Chemistry, 2000, vol. 38, # 6, p. 468 - 471