SB-247386

Chemical Name: (3aS,4R,5S,6S,8R,9R,9aR,10R)-N-(Quinuclidin-4-ylcarbonyl)carbamic acid 5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
CAS No. 193535-63-6
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线:The reaction of quinuclidine-4-carboxylic acid (I) with refluxing SOCl2 gives the corresponding acyl chloride (II),which is treated with silver cyanate in dichloromethane yielding intermediate (II).The condensation of (III) with 3-deoxo-11-deoxy-3(R)-methoxy-11-oxo-4-epi-mutilin (IV) and triethylamine in dichloromethane affords the corresponding carbamate (V),which is finally rearranged by a treatment with con.HCl in dioxane.

合成路线:Ethyl (3R,4S)-1-azabicyclo[2.2.1]heptane-3-carboxylate (I) was hydrolyzed in boiling HCl,and the resulting acid (II) was further converted to acid chloride (III) by treatment with SOCl2.Condensation of acid chloride (III) with (3R)-3-deoxo-11-deoxy-3-methoxy-11-oxo-4-epimutilin (IV) in the presence of silver cyanate furnished the acylcarbamate ester (V).Acid-promoted rearrangement of (V) to the mutilin acylcarbamate then gave the title compound,which was isolated as the corresponding hydrochloride salt.