S-15261

Chemical Name: L-4-[2-[2-(9-Fluorenyl)acetamido]ethyl]benzoic acid 2-[2-methoxy-2-[3-(trifluoromethyl)phenyl]ethylamino]ethyl ester
CAS No. 159978-02-6, 147308-18-7 ((+)-enantiomer, monoHCl), 147308-15-4 (monoHCl), 147308-19-8 (monoHCl salt, racemic)
项目整合开发状态: Phase II
项目研究机构: Servier (Originator)
合成路线:3-Bromobenzotrifluoride (I) is converted into the corresponding Grignard reagent (II),which is then condensed with 1,2-dibromo-1-methoxyethane (III) producing the phenethyl bromide (IV).Reaction of bromide (IV) with (S)-alpha-methylbenzylamine (V) yields amine (VI) as a diastereomeric mixture.Recrystallization of (VI) from isopropanol leads to a pure diastereoisomer,which is subsequently treated with ethyl bromoacetate to furnish amino ester (VII).Reduction of (VII) using LiAlH4 provides alcohol (VIII),and further chlorination with SOCl2 leads to chloro amine (IX).Acid (X) is then alkylated with chloride (IX) producing ester (XI).The chiral auxiliary alpha-methylbenzyl group is finally removed by hydrogenolysis to afford the title compound.