Droxidopa, DOPS(L-threo), Dops
屈西多巴Chemical Name: (-)-threo-beta,3-Dihydroxy-L-tyrosine; (-)-threo-3-(3,4-Dihydroxyphenyl)-L-serine; (-)-(2S,3R)-2-Amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid
CAS No. 23651-95-8
项目整合开发状态: Launched-1989
项目研究机构: Sumitomo Pharmaceuticals (Originator)
合成路线:The condensation of 3,4-dimethoxybenzaldehyde (I) with glycine (II) by means of KOH in hot methanol gives racemic threo-3-(3,4-dimethoxyphenyl)serine (III),which is acylated with N-(ethoxycarbonyl)phthalimide (IV) by means of Na2CO3 in water yielding the corresponding N-phthaloyl derivative (V).The reaction of (V) with AlCl3 and ethyl mercaptan in dichloromethane affords N-phthaloyl-3-(3,4-dihydroxyphenyl)serine (VI),which is deprotected with hydrazine in refluxing ethanol to racemic threo-3-(3,4-dihydroxyphenyl)serine (VII).The resolution of the racemic form (VII) is performed through its benzyloxy derivative.
📌 参考资料/链接：
参考文献标题:Process for the production of optically active thr
文献作者:Ohashi,N.; Nagata,S.; Ishimuzi,K.; Katsube,J.(Sumitomo Pharmaceuticals Co.,Ltd.)
参考来源:EP 0024210; US 4319040
📄 详细内容
合成路线:The condensation of 3,4-dimethoxybenzaldehyde (I) with glycine (II) by means of KOH in hot methanol gives racemic threo-3-(3,4-dimethoxyphenyl)serine (III),which is acylated with N-(ethoxycarbonyl)phthalimide (IV) by means of Na2CO3 in water yielding the corresponding N-phthaloyl derivative (V).The reaction of (V) with AlCl3 and ethyl mercaptan in dichloromethane affords N-phthaloyl-3-(3,4-dihydroxyphenyl)serine (VI),which is deprotected with hydrazine in refluxing ethanol to racemic threo-3-(3,4-dihydroxyphenyl)serine (VII).The resolution of the racemic form (VII) is performed through its benzyloxy derivative.
参考文献标题:Process for producing 3-(3,4-dihydroxyphenyl)serin
文献作者:Ohashi,N.; Nagata,S.; Ishizumi,K.(Sumitomo Pharmaceuticals Co.,Ltd.)
参考来源:EP 0128684; US 4562263
合成路线:The condensation of 3,4-dimethoxybenzaldehyde (I) with glycine (II) by means of KOH in hot methanol gives racemic threo-3-(3,4-dimethoxyphenyl)serine (III),which is acylated with N-(ethoxycarbonyl)phthalimide (IV) by means of Na2CO3 in water yielding the corresponding N-phthaloyl derivative (V).The reaction of (V) with AlCl3 and ethyl mercaptan in dichloromethane affords N-phthaloyl-3-(3,4-dihydroxyphenyl)serine (VI),which is deprotected with hydrazine in refluxing ethanol to racemic threo-3-(3,4-dihydroxyphenyl)serine (VII).The resolution of the racemic form (VII) is performed through its benzyloxy derivative.
参考文献标题:L-threo-DOPS
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1987,12(5),433
产品链接: CAS No. 23651-95-8››