S-31354

Chemical Name: 3-[6-(4-Chlorophenylsulfonamido)-2-(2-nitrooxyethyl)-5,6,7,8-tetrahydro-1-naphthyl]propionic acid
CAS No. 213313-90-7
项目整合开发状态: Preclinical
项目研究机构: Servier (Originator)
合成路线:Diels-Alder condensation of benzopyran (I) with methyl (trimethylsilyl)propynoate (II) gave rise to tetrahydronaphthalene (III).After reduction of the ester group of (III) with LiAlH4,the resulting alcohol (IV) was further oxidized to aldehyde (V) by means of 4-benzylpyridinium dichromate.Treatment of (V) with iodine monochloride produced iodonaphthalene (VI).Subsequent reaction of (VI) with vinyl tributyltin and palladium tetrakis(triphenylphosphine) yielded the vinyl naphthalene (VII).Wittig reaction of (VIII with (carbomethoxymethylidene)triphenylphosphorane (VIII) gave the arylpropenoate ester (IX),which was reduced to the saturated ester (X) employing samarium iodide.

合成路线:Hydroboration of the vinyl group of (X),followed by oxidative treatment with sodium perborate furnished alcohol (XI),which was further activated as the corresponding tosylate (XII).Displacement of the tosylate group of (XII) with tetrabutylammonium nitrate in toluene gave nitrate ester (XIII).The methyl ester group of (XIII) was finally hydrolyzed with NaOH to the target carboxylic acid.