methyl (E)-5-(hydroxyimino)-4-oxo-2-pentenoate -Drug Synthesis Database

【结构式】

【分子编号】59144

【品名】methyl (E)-5-(hydroxyimino)-4-oxo-2-pentenoate

【CA登记号】

【分子式】C₆H₇NO₄

【分子量】157.12592

【元素组成】C 45.87% H 4.49% N 8.91% O 40.73%

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：(IV)

Methyl acetylacrylate (III) was obtained by bromination of methyl levulinate (I) followed by dehydrohalogenation of the resultant bromide (II). Isonitrosation of ketone (III) by means of ethyl nitrite in ethereal HCl produced the alpha-keto oxime (IV). Reduction of oxime (IV) and simultaneous ester hydrolysis by means of Sn/SnCl2 in concentrated HCl led to the target 5-aminolevulinic acid.

参考文献中间体

合成目标

【1】 Corwin, A.H.; Wynn, R.W.; The hydrogenation of oxaloacetone. A new synthesis of beta-thiolimidazolylpropionic acid. J Org Chem 1950, 15, 203.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	50960	Methyl levulinate	C₆H₁₀O₃	详情	详情
(II)	59142	methyl 2-bromo-4-oxopentanoate	C₆H₉BrO₃	详情	详情
(III)	59143	Methyl trans-beta-acetylacrylate; Methyl trans-4-oxo-2-pentenoate	C₆H₈O₃	详情	详情
(IV)	59144	methyl (E)-5-(hydroxyimino)-4-oxo-2-pentenoate	C₆H₇NO₄	详情	详情

Extended Information