BTA-243, CL-316243(former code)

Chemical Name: (R,R)-5-[2-[2-(3-Chlorophenyl)-2-hydroxyethylamino]propyl]-1,3-benzodioxole-2,2-dicarboxylic acid disodium salt
CAS No. 138908-40-4, 138908-41-5 ((S, S)-isomer), 151126-84-0 (CL-316243), 139014-45-2 (racemate)
项目整合开发状态: Phase II
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:The chiral synthesis of CL 316,243 is described:The chiral epoxide (IV) was prepared in a three-step procedure starting from 3-chloroacetophenone.Monochlorination followed by asymmetric reduction gave the chiral chlorohydrin (III),which was treated with base to give the epoxide.The chiral amine was prepared in a six step sequence starting from L-DOPA.Protection of the amine followed by permethylation and ester reduction gave the alcohol (VIII).Conversion to the mesylate followed by catalytic hydrogenation gave enantiomerically pure amine (X).Reaction of the epoxide (IV) with the amine (X) gave the phenethanolamine (XI).Protection as the oxazolidinone (XII) followed by demethylation and subsequent malonation with diethyl dibromomalonate yielded the protected diester (XIV).Basic hydrolysis followed by reverse phase chromatography gave CL 316,243.