methyl (3S,4S)-3-amino-4-hydroxy-4-phenylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】31784

【品名】methyl (3S,4S)-3-amino-4-hydroxy-4-phenylbutanoate

【CA登记号】

【分子式】C₁₁H₁₅NO₃

【分子量】209.24504

【元素组成】C 63.14% H 7.23% N 6.69% O 22.94%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XVII)

In a different approach, starting from the chiral oxazolidine (XV), conversion to the corresponding mesylate and further displacement by NaCN afforded nitrile (XVI). Acid hydrolysis of the oxazolidine (XVI) and esterification with MeOH produced aminoester (XVII). This was acylated with acid chloride (II) to yield a mixture of amide-ester (XVIII) and amide-lactone (XIX). Reduction of this mixture with NaBH4 and AcOH furnished diol (XX), which was cyclized employing BF3 in methanesulfonic acid. The resulting benzazepine (XXI) was reductively methylated under Schweiler-Clarke conditions to give (XIV). Finally, chlorination with PCl5, followed by cyclization and demethylation with AlCl3 provided the title compound.

参考文献中间体

合成目标

【1】 Wu, G.; et al.; Amino diol based asymetric syntheses of a fused benzazepine as a selective D1 dopamine receptor. Org Process Res Dev 1997, 1, 5, 359.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	31769	2-(3-chloro-4-methoxyphenyl)acetyl chloride		C₉H₈Cl₂O₂	详情	详情
(XIV)	31781	2-[(1R,2S)-7-chloro-8-methoxy-3-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-yl]-1-ethanol		C₂₀H₂₄ClNO₂	详情	详情
(XV)	31782	[(4S,5S)-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol	53732-41-5	C₁₁H₁₃NO₂	详情	详情
(XVI)	31783	2-[(4S,5S)-2-methyl-5-phenyl-4,5-dihydro-1,3-oxazol-4-yl]acetonitrile		C₁₂H₁₂N₂O	详情	详情
(XVII)	31784	methyl (3S,4S)-3-amino-4-hydroxy-4-phenylbutanoate		C₁₁H₁₅NO₃	详情	详情
(XVIII)	31785	methyl (3S,4S)-3-[[2-(3-chloro-4-methoxyphenyl)acetyl]amino]-4-hydroxy-4-phenylbutanoate		C₂₀H₂₂ClNO₅	详情	详情
(XIX)	31786	2-(3-chloro-4-methoxyphenyl)-N-[(2R,3S)-5-oxo-2-phenyltetrahydro-3-furanyl]acetamide		C₁₉H₁₈ClNO₄	详情	详情
(XX)	31787	(1S,2S)-2-[(3-chloro-4-methoxyphenethyl)amino]-1-phenyl-1,4-butanediol		C₁₉H₂₄ClNO₃	详情	详情
(XXI)	31788	2-[(1R,2S)-7-chloro-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-yl]-1-ethanol		C₁₉H₂₂ClNO₂	详情	详情

Extended Information