Tiropramide Explained

Tiropramide is the International nonproprietary name of an antispasmodic drug.^[1]

Synthesis

The acylation of racemic tyrosine (1) with benzoyl chloride gives N,O-dibenzoyl-tyrosine (2). Amide formation with dipropylamine (3) using the mixed anhydride method gives the intermediate (4). Hydrolysis of the phenolic ester with sodium hydroxide forms (5), which is alkylated with to produce the ether tiropramide.^{[2] [3]}

Notes and References

1. Vidal y Plana RR, Cifarelli A, Setnikar I . Mechanism of smooth muscle relaxation by tiropramide . The Journal of Pharmacy and Pharmacology . 33 . 1 . 19–24 . January 1981 . 6114146 . 10.1111/j.2042-7158.1981.tb13694.x . 22487894 .
2. Francesco Makovec, Luigi Rovati, Paolo Senin, (1977 to Rotta Research Laboratorium S.P.A.)
3. Web site: Tiropramide . Thieme . 2024-07-01 .