tert-butyl (1S)-1-(4-fluorobenzyl)-2-(4-hydroxy-1-piperidinyl)-2-oxoethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】25930

【品名】tert-butyl (1S)-1-(4-fluorobenzyl)-2-(4-hydroxy-1-piperidinyl)-2-oxoethylcarbamate

【CA登记号】

【分子式】C₁₉H₂₇FN₂O₄

【分子量】366.4328632

【元素组成】C 62.28% H 7.43% F 5.18% N 7.64% O 17.47%

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：(III)

The reaction of N-(tert-butoxycarbonyl)-L-4-fluorophenylalanine (I) with 4-hydroxypiperidine (II) by means of triethylamine, EDC and HOBT in dichloromethane gives the expected piperidide (III), which is deprotected with with HCl in dioxane to afford (IV) with a free amino group that is condensed with 5-chloro-1H-indole-2-carboxylic acid (V) by means of triethylamine, EDC and HOBT as before.

参考文献中间体

合成目标

【1】 Hoover, D.J.; et al.; Indole-2-carboxamide inhibitors of human liver glycogen phosphorylase. J Med Chem 1998, 41, 16, 2934.
【2】 Hulin, B.; Hoover, D.J.; Treadway, J.L.; Martin, W.H.; Phillips, D. (Pfizer Inc.); Substd. N-(indole-2-carbonyl)-glycinamides and derivs. as glycogen phosphorylase inhibitors. EP 0832065; WO 9639384 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	25929	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-fluorophenyl)propionic acid		C₁₄H₁₈FNO₄	详情	详情
(II)	12076	4-Piperidinol; 4-Hydroxypiperidine	5382-16-1	C₅H₁₁NO	详情	详情
(III)	25930	tert-butyl (1S)-1-(4-fluorobenzyl)-2-(4-hydroxy-1-piperidinyl)-2-oxoethylcarbamate		C₁₉H₂₇FN₂O₄	详情	详情
(IV)	25931	(2S)-2-amino-3-(4-fluorophenyl)-1-(4-hydroxy-1-piperidinyl)-1-propanone		C₁₄H₁₉FN₂O₂	详情	详情
(V)	25932	5-Chloroindole-2-carboxylic acid; 5-Chloro-1H-indole-2-carboxylic acid	10517-21-2	C₉H₆ClNO₂	详情	详情

Extended Information