BMS-292655
Chemical Name: 3-(Phosphonooxymethyl)benzoic acid [2(R)-[4-(4-cyanophenyl)thiazol-2-yl]-1(R)-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-ylmethyl)propoxy]methyl ester sodium salt
CAS No. 271250-73-8, 271250-72-7 (free acid)
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The condensation of BMS-207147 (I) with 3-(chloromethyl)benzoic acid chloromethyl ester (II) (obtained by esterification of 3-(chloromethyl)benzoyl chloride (III) with paraformaldehyde and ZnCl2) by means of KH in THF gives the adduct (IV),which is condensed with phosphoric acid di-tert-butyl ester (V) to yield the phosphate (V).Finally,this compound is hydrolyzed with TFA in dichloromethane and treated with NaHCO3 to provide the target sodium salt.
📌 参考资料/链接：
参考文献标题:Water soluble prodrugs of azole cpds.
文献作者:Hudyma,T.W.; Kim,O.K.; Zheng,X.(Bristol-Myers Squibb Co.)
参考来源:WO 0030655
📄 详细内容
合成路线:The condensation of BMS-207147 (I) with 3-(chloromethyl)benzoic acid chloromethyl ester (II) (obtained by esterification of 3-(chloromethyl)benzoyl chloride (III) with paraformaldehyde and ZnCl2) by means of KH in THF gives the adduct (IV),which is condensed with phosphoric acid di-tert-butyl ester (V) to yield the phosphate (V).Finally,this compound is hydrolyzed with TFA in dichloromethane and treated with NaHCO3 to provide the target sodium salt.
参考文献标题:BMS-292655,a soluble prodrug of the clinically efficacious antifungal triazole,BMS-207147 (ravuconazole)
文献作者:Hudyma,T.W.; Zheng,X.; Clark,J.; et al.
参考来源:42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002,San Diego) 2002,Abst F-816