benzyl 3-oxobutanoate -Drug Synthesis Database

【结构式】

【分子编号】65102

【品名】benzyl 3-oxobutanoate

【CA登记号】

【分子式】C₁₁H₁₂O₃

【分子量】192.21448

【元素组成】C 68.74% H 6.29% O 24.97%

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)

Nitrosation of tert-butyl acetoacetate (I) with NaNO2 in cold AcOH leads to oxime (II), which is further condensed with benzyl acetoacetate (III) in the presence of Zn and ammonium acetate, to produce pyrrole (IV). The 4-benzyl ester of (IV) is selectively removed by catalytic hydrogenolysis over Pd/C, yielding the pyrrole-4-carboxylic acid (V). Subsequent coupling of acid (V) with 3,3-dimethyl-2-butanol (VI) employing trifluoroacetic anhydride furnishes the target pyrrole diester.

参考文献中间体

合成目标

【1】 Synthesis and pharmacological characterisation of 2,4-dicarboxy-pyrroles as selective non-competitive mGluR1 antagonists. Bioorg Med Chem 2003, 11, 2, 171.

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)	27907	Acetoacetic acid tert-butyl ester;3-Oxo-butanoic acid 1,1-dimethylethyl estertert-butyl 3-oxobutanoate	1694-31-1	C₈H₁₄O₃	详情	详情
(II)	63353	1,1-dimethylethyl 2-(hydroxyimino)-3-oxobutanoate	14352-65-9	C₈H₁₃NO₄	详情	详情
(III)	65102	benzyl 3-oxobutanoate		C₁₁H₁₂O₃	详情	详情
(IV)	65101	4-benzyl 2-(tert-butyl) 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate		C₁₉H₂₃NO₄	详情	详情
(V)	65100	5-(tert-butoxycarbonyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid		C₁₂H₁₇NO₄	详情	详情
(VI)	65099	3,3-dimethyl-2-butanol		C₆H₁₄O	详情	详情

Extended Information