New synthesis of (RS)-carnitine chloride.
A four-step synthesis of (RS)-carnitine chloride was developed using extremely mild reaction conditions and versatile intermediates. Crotyl chloride was converted to tert-butyl 3-butenoate using tert-butyl alcohol and triethylamine in ether. Treatment of tert-butyl 3-butenoate with m-chloroperbenzoic acid in chloroform afforded tert-butyl 3,4-epoxybutyrate. Reaction of this compound with trimethylamine hydrochloride in methanol, followed by mild acid hydrolysis of the tert-butyl ester, afforded (RS)-carnitine chloride.
D002331:Carnitine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D006885:Hydroxybutyrates / Q000138:chemical synthesis; D008722:Methods
D006885:Hydroxybutyrates; D002331:Carnitine