tert-butyl 3-(5-hydroxy-1-naphthyl)propanoate -Drug Synthesis Database

【结构式】

【分子编号】26497

【品名】tert-butyl 3-(5-hydroxy-1-naphthyl)propanoate

【CA登记号】

【分子式】C₁₇H₂₀O₃

【分子量】272.344

【元素组成】C 74.97% H 7.4% O 17.62%

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：(I)

Alkylation of tert-butyl (5-hydroxy-2-naphthyl)propionate (I) with methyl bromoacetate (II) in the presence of K2CO3 provided ether (III). Subsequent deprotection of the tert-butyl ester of (III) using trifluoroacetic acid in CH2Cl2 gave carboxylic acid (IV). This was coupled to benzhydrylamine in the presence of EDC and DMAP to afford amide (VI). Finally, ester hydrolysis of (IV) with NaOH yielded the target compound.

参考文献中间体

合成目标

【1】 Nagao, Y.; Torisu, K.; Maruyama, T. (Ono Pharmaceutical Co., Ltd.); Naphthyloxyacetic acid derivs. and their use as PGE2 agonists and antagonists. EP 0719760; JP 1996239356 .

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)	26497	tert-butyl 3-(5-hydroxy-1-naphthyl)propanoate		C₁₇H₂₀O₃	详情	详情
(II)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情
(III)	26498	tert-butyl 3-[5-(2-methoxy-2-oxoethoxy)-1-naphthyl]propanoate		C₂₀H₂₄O₅	详情	详情
(IV)	26499	3-[5-(2-methoxy-2-oxoethoxy)-1-naphthyl]propionic acid		C₁₆H₁₆O₅	详情	详情
(V)	15149	alpha-Aminodiphenylmethane; diphenylmethanamine; benzhydrylamine	91-00-9	C₁₃H₁₃N	详情	详情
(VI)	26500	methyl 2-([5-[3-(benzhydrylamino)-3-oxopropyl]-1-naphthyl]oxy)acetate		C₂₉H₂₇NO₄	详情	详情

Extended Information