Osutidine, T-593
Chemical Name: (?-1-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]-2-(methylsulfonyl)-3-[2-[5-(methylaminomethyl)furan-2-ylmethylthio]ethyl]guanidine
CAS No. 140695-21-2, 123280-14-8 ((R)-isomer), 123280-13-7 ((S)-isomer), 123280-17-1 (undefined isomer)
项目整合开发状态: Phase III
项目研究机构: Toyama (Originator)
合成路线:The acylation of 5-(methylaminomethyl)furan-2-methanol (I) with 2,2,2-trichloroethyl chloroformate (II) and pyridine in dichloromethane gives the corresponding N-acyl derivative (III),which is condensed with 2-mercaptoethylamine (IV) by means of sodium methoxide in methanol to yield the thioether (V).The condensation of (V) with diphenyl methanesulfonimidocarbonate (VI) and 2-hydroxy-2-(4-hydroxyphenyl)ethylamine (VII) by means of potassium acetate and triethylamine in acetonitrile - propanol affords the protected final product (VIII),which is finally deprotected by treatment with activated Zn and potassium dihydrogen phosphate.
📌 参考资料/链接：
参考文献标题:Amine deriv.and its salts and antiulcer agent containing the same
文献作者:Hirai,S.; Hirano,H.; Arai,H.; Shibata,H.; Kusayanagi,Y.; Hashiba,K.(Toyama Chemical Co.,Ltd.)
参考来源:CH 675244; DE 3828869; US 4871765
📄 详细内容
合成路线:The acylation of 5-(methylaminomethyl)furan-2-methanol (I) with 2,2,2-trichloroethyl chloroformate (II) and pyridine in dichloromethane gives the corresponding N-acyl derivative (III),which is condensed with 2-mercaptoethylamine (IV) by means of sodium methoxide in methanol to yield the thioether (V).The condensation of (V) with diphenyl methanesulfonimidocarbonate (VI) and 2-hydroxy-2-(4-hydroxyphenyl)ethylamine (VII) by means of potassium acetate and triethylamine in acetonitrile - propanol affords the protected final product (VIII),which is finally deprotected by treatment with activated Zn and potassium dihydrogen phosphate.
参考文献标题:T-593
文献作者:Castar,J.; Prous,J.; Mealy,N.
参考来源:Drugs Fut 1993,18(9),809
合成路线:The acylation of 5-(methylaminomethyl)furan-2-methanol (I) with 2,2,2-trichloroethyl chloroformate (II) and pyridine in dichloromethane gives the corresponding N-acyl derivative (III),which is condensed with 2-mercaptoethylamine (IV) by means of sodium methoxide in methanol to yield the thioether (V).The condensation of (V) with diphenyl methanesulfonimidocarbonate (VI) and 2-hydroxy-2-(4-hydroxyphenyl)ethylamine (VII) by means of potassium acetate and triethylamine in acetonitrile - propanol affords the protected final product (VIII),which is finally deprotected by treatment with activated Zn and potassium dihydrogen phosphate.
参考文献标题:Synthesis of beta-hydroxyphenethyl-based compounds and their physico-chemical properties and structural features
文献作者:Shibata,H.; Hirai,N.; Kusayanagi,K.; Arai,H.; Hirano,H.
参考来源:113th Annu Meet Pharmaceut Soc Jpn (March 29-31,Osaka) 1993,Abst 29PB 10-28