ethyl 2-[4-(4-chloro-4-oxobutyl)phenoxy]-2-methylpropanoate -Drug Synthesis Database

【结构式】

【分子编号】57590

【品名】ethyl 2-[4-(4-chloro-4-oxobutyl)phenoxy]-2-methylpropanoate

【CA登记号】

【分子式】C₁₆H₂₁ClO₄

【分子量】312.79304

【元素组成】C 61.44% H 6.77% Cl 11.33% O 20.46%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

In an alternative method, 4-(4-methoxyphenyl)butyric acid (I) is demethylated to phenol (II) by heating at 190 C with pyridine hydrochloride. Alkylation of phenol (II) with ethyl 2-bromoisobutyrate (III) gives ether (IV). The carboxyl group of (IV) is then activated as the corresponding acid chloride (V) by treatment with oxalyl chloride in the presence of DMF.

参考文献中间体

合成目标

【1】 Braden, T.; et al.; Novel acid-catalyzed synthesis of triazolones from acyl semicarbazides. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 381.
【2】 Perixosome proliferator activated receptor alpha agonists. WO 0238553 .

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)	57587	4-(4-Methoxyphenyl)butyric acid		C₁₁H₁₄O₃	详情	详情
(II)	57588	4-(4-hydroxyphenyl)butanoic acid		C₁₀H₁₂O₃	详情	详情
(III)	39799	ethyl 2-bromo-2-methylpropanoate	600-00-0	C₆H₁₁BrO₂	详情	详情
(IV)	57589	4-[4-(2-ethoxy-1,1-dimethyl-2-oxoethoxy)phenyl]butanoic acid		C₁₆H₂₂O₅	详情	详情
(V)	57590	ethyl 2-[4-(4-chloro-4-oxobutyl)phenoxy]-2-methylpropanoate		C₁₆H₂₁ClO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Reductive alkylation of tert-butyl carbazate (VI) with 4-methylbenzaldehyde (VII) under catalytic hydrogenation conditions affords the N-p-methylbenzyl carbazate (VIII). This is then condensed with trimethylsilyl isocyanate to form the semicarbazide derivative (IX). Subsequent acidic Boc group cleavage in (IX) yields (X). Semicarbazide (X) is then acylated with acid chloride (V) producing (XI). Cyclization of the acyl semicarbazide (XI) in the presence of CSA leads to triazolone (XII). Finally, alkaline hydrolysis of the ethyl ester group of (XII) furnishes the title carboxylic acid.

参考文献中间体

合成目标

【1】 Braden, T.; et al.; Novel acid-catalyzed synthesis of triazolones from acyl semicarbazides. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 381.
【2】 Perixosome proliferator activated receptor alpha agonists. WO 0238553 .

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)	57590	ethyl 2-[4-(4-chloro-4-oxobutyl)phenoxy]-2-methylpropanoate		C₁₆H₂₁ClO₄	详情	详情
(VI)	10893	tert-butyl 1-hydrazinecarboxylate; tert-butyl carbazate	870-46-2	C₅H₁₂N₂O₂	详情	详情
(VII)	10161	4-Methylbenzaldehyde	104-87-0	C₈H₈O	详情	详情
(VIII)	57591	tert-butyl 2-(4-methylbenzyl)-1-hydrazinecarboxylate		C₁₃H₂₀N₂O₂	详情	详情
(IX)	57592	tert-butyl 2-(aminocarbonyl)-2-(4-methylbenzyl)-1-hydrazinecarboxylate		C₁₄H₂₁N₃O₃	详情	详情
(X)	57593	1-(4-methylbenzyl)-1-hydrazinecarboxamide		C₉H₁₃N₃O	详情	详情
(XI)	57594	ethyl 2-(4-{4-[2-(aminocarbonyl)-2-(4-methylbenzyl)hydrazino]-4-oxobutyl}phenoxy)-2-methylpropanoate		C₂₅H₃₃N₃O₅	详情	详情
(XII)	57595	ethyl 2-methyl-2-(4-{3-[1-(4-methylbenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]propyl}phenoxy)propanoate		C₂₅H₃₁N₃O₄	详情	详情

Extended Information