【药物名称】Droxidopa, DOPS(L-threo), Dops
化学结构式(Chemical Structure):
参考文献No.4708
标题:Process for the production of optically active thr
作者:Ohashi, N.; Nagata, S.; Ishimuzi, K.; Katsube, J. (Sumitomo Pharmaceuticals Co., Ltd.)
来源:EP 0024210; US 4319040
合成路线图解说明:

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No.4709
标题:Process for producing 3-(3,4-dihydroxyphenyl)serin
作者:Ohashi, N.; Nagata, S.; Ishizumi, K. (Sumitomo Pharmaceuticals Co., Ltd.)
来源:EP 0128684; US 4562263
合成路线图解说明:

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No.55426
标题:L-threo-DOPS
作者:Casta馿r, J.; Prous, J.
来源:Drugs Fut 1987,12(5),433
合成路线图解说明:

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.

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