(2S,3S)-3-amino-1-chloro-4-phenyl-2-butanol -Drug Synthesis Database

【结构式】

【分子编号】19742

【品名】(2S,3S)-3-amino-1-chloro-4-phenyl-2-butanol

【CA登记号】

【分子式】C₁₀H₁₄ClNO

【分子量】199.68

【元素组成】C 60.15% H 7.07% Cl 17.75% N 7.01% O 8.01%

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)

Palinavir can also be obtained as follows: The controlled oxidation of 2(S)-(dibenzylamino)-3-phenyl-1-propanol (XIII) with pyridine-SO3 complex in DMSO gives the corresponding aldehyde (XIV), which is condensed with bromochloromethane (XV) by means of Li in THF followed by hydrolysis with HCl yielding regioselectively the 1-chloro-2-butanol (XVI). The debenzylation of (XVI) by hydrogenation over Pd/C affords the free amine (XVII), which is treated with tert-butoxycarbonyl anhydride/triethylamine and dehydrochlorinated with KOH in methanol to give the desired chiral epoxide (V).

参考文献中间体

合成目标

【1】 Beaulieu, P.L.; et al.; Practical, stereoselective synthesis of palinavir, a potent HIV protease inhibitor. J Org Chem 1997, 62, 11, 3440.
【2】 Gillard, J.; et al.; Preparation of (2S,4R)-4-hydroxypipecolic acid and derivatives. J Org Chem 1996, 61, 6, 2226.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	19730	tert-butyl (1S)-1-[(2S)oxiranyl]-2-phenylethylcarbamate	98737-29-2	C₁₅H₂₁NO₃	详情	详情
(XIII)	19738	(2S)-2-[bis(4-methylphenyl)amino]-3-phenyl-1-propanol		C₂₃H₂₅NO	详情	详情
(XIV)	19739	(2S)-2-[bis(4-methylphenyl)amino]-3-phenylpropanal		C₂₃H₂₃NO	详情	详情
(XV)	19740	bromo(chloro)methane	74-97-5	CH₂BrCl	详情	详情
(XVI)	19741	(2S,3S)-3-[bis(4-methylphenyl)amino]-1-chloro-4-phenyl-2-butanol		C₂₄H₂₆ClNO	详情	详情
(XVII)	19742	(2S,3S)-3-amino-1-chloro-4-phenyl-2-butanol		C₁₀H₁₄ClNO	详情	详情

Extended Information