A facile synthesis of beta-(S-benzylmercapto)-beta, beta-cyclopentamethylene-propionic acid.
The title compound is a key intermediate for the preparation of oxytocin and vasopressin antagonists. Using sodium benzylmercaptide instead of boron trifluoride etherate as catalyst gives a better than four fold overall improvement in yield of the title compound from ethyl cyclohexylideneacetate and benzylmercaptan. The preparation of the corresponding acid labile S-p-methylbenzylmercapto and S-p-methoxybenzylmercapto analogs is also described.
D055598:Chemical Phenomena; D002621:Chemistry; D003517:Cyclopentanes / Q000138:chemical synthesis*; D014667:Vasopressins / Q000037:antagonists & inhibitors
D003517:Cyclopentanes; D014667:Vasopressins; C038605:beta-(S-benzylmercapto)-beta,beta-cyclopentamethylenepropionic acid