新产品编号:73281
Chemical Name: (-)-3-[4-[2-[N-(2-Benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2(S)-methoxypropionic acid
CAS No. 158062-26-1
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Rhodium acetate-mediated insertion of methanol into diazotyrosine methyl ester (I) provided the alpha-methoxy ester (IIa-b).Subsequent alkylation of (IIa-b) with mesylate (III) using NaH in DMF gave the racemic adduct (IVa-b).Finally,kinetic resolution of (Va-b) employing the lipase from Rhizopus delemar at a pH of 7.0 produced the desired (S)-acid while leaving the unchanged (R)-ester (V).
📌 参考资料/链接：
参考文献标题:Heterocyclic cpds.as pharmaceutical
文献作者:Haigh,D.; Sime,J.(SmithKline Beecham plc)
参考来源:EP 1000938; US 5869495; US 6048883; WO 9401420
📄 详细内容
合成路线:Rhodium acetate-mediated insertion of methanol into diazotyrosine methyl ester (I) provided the alpha-methoxy ester (IIa-b).Subsequent alkylation of (IIa-b) with mesylate (III) using NaH in DMF gave the racemic adduct (IVa-b).Finally,kinetic resolution of (Va-b) employing the lipase from Rhizopus delemar at a pH of 7.0 produced the desired (S)-acid while leaving the unchanged (R)-ester (V).
参考文献标题:Non-thiazolidinedione antihyperglycaemic agents.Part 3: The effects of stereochemistry on the potency of alpha-methoxy-beta-phenylpropanoic acids
文献作者:Haigh,D.; Allen,G.; Birrell,H.C.; Buckle,D.R.; Cantello,B.C.; Eggleston,D.S.; Haltiwanger,R.C.; Holder,J.C.; Lister,C.A.; Pinto,I.L.; Rami,H.K.; Sime,J.T.; Smith,S.A.; Sweeney,J.D.
参考来源:Bioorg Med Chem 1999,7(5),821