Candoxatril, UK-79300

坎沙曲 坎沙曲 Chemical Name: (alphaS)-1-[(cis-4-Carboxycyclohexyl)carbamoyl]-alpha-[(2-methoxyethoxy)methyl]cyclopentanepropionic acid,alpha-5-indanyl ester; cis-4-[1-[(S)-2-(Indan-5-yloxycarbonyl)-3-(2-methoxyethoxy)propyl]cyclopentylcarbonylamino]cyclohexanecarboxylic acid
CAS No. 123122-55-4, 118785-03-8 (undefined stereoch.)
项目整合开发状态: Phase III
项目研究机构: Pfizer (Originator)
合成路线:The known 2-(2-methoxyethoxymethyl)-3-[1-(phenacyloxycarbonyl)cyclopentyl]propanoic acid (I) was esterified with 5-indanol (II) by using EDC and HOBt to afford the indanyl ester (III).The phenacyl ester group was then reductively cleaved with Zn in HOAc to yield the racemic carboxylic acid (IV).Resolution of (IV) by means of (+)-pseudoephedrine provided the (S)-enantiomer (V).The chiral acid (V) was then coupled with benzyl cis-4-amino-1-cyclohexancarboxylate (VI) in the presence of EDC and HOBt to furnish amide (VII).The benzyl ester group of (VII) was finally cleaved by hydrogenolysis over Pd/C to give the title compound.