INT-747, 6-ECDCA

奥贝胆酸Chemical Name: (3alpha,5beta,6alpha,7alpha)-6-Ethyl-3,7-dihydroxycholan-24-oic acid; 6-Ethylchenodeoxycholic acid
CAS No. 459789-99-2
项目整合开发状态: Preclinical
项目研究机构: Universit?degli Studi di Perugia (Originator), Intercept Pharmaceuticals (Licensee), GlaxoSmithKline (Codevelopment)
合成路线:7-Oxo-lithocholic acid (I) is protected as the tetrahydropyranyl ether (II) using dihydropyran in the presence of p-toluenesulfonic acid.Diastereoselective alkylation at the alpha-position of the keto group of (II) with ethyl bromide and LDA provides (III).Then,simultaneous esterification and tetrahydropyranyl group removal in (III) with methanolic HCl leads to methyl ester (IV).Subsequent ketone (IV) reduction with NaBH4 furnishes the 7-alpha alcohol (V).Finally,basic hydrolysis of the methyl ester group of (V) provides the corresponding carboxylic acid.