Methyl levulinate -Drug Synthesis Database

【结构式】

【分子编号】50960

【品名】Methyl levulinate

【CA登记号】

【分子式】C₆H₁₀O₃

【分子量】130.1436

【元素组成】C 55.37% H 7.74% O 36.88%

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：(I)

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

合成路线2

该中间体在本合成路线中的序号：(VII)

The reaction of phenol (I) with 4-oxopentanoic acid (II) by means of H2SO4 gives 4,4-bis(4-hydroxyphenyl)pentanoic acid (III), which is esterified with MeOH and H2SO4 to yield the methyl pentanoate (IV). The condensation of (IV) with 2-(chloromethyl)quinoline (V) by means of K2CO3 in DMF affords the adduct (VI), which is finally hydrolyzed with NaOH in methanol/dioxane to provide the target sodium salt. Alternatively, the intermediate methyl pentanoate (IV) can also be obtained by direct condensation of phenol (I) with methyl 4-oxopentanoate (VII) by means of H2SO4 as before.

参考文献中间体

合成目标

【1】 Gunn, D.E.; Bhatia, P.; Kolasa, T.; et al.; Symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as inhibitors of leukotriene biosynthesis. J Med Chem 2000, 43, 17, 3322.

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)	23540	Phenol	108-95-2	C₆H₆O	详情	详情
(II)	36170	4-oxopentanoic acid	123-76-2	C₅H₈O₃	详情	详情
(III)	22391	4,4-bis(4-hydroxyphenyl)pentanoic acid	126-00-1	C₁₇H₁₈O₄	详情	详情
(IV)	22392	methyl 4,4-bis(4-hydroxyphenyl)pentanoate		C₁₈H₂₀O₄	详情	详情
(V)	13162	2-(Chloromethyl)quinoline; alpha-Chloroquinaldine	4377-41-7	C₁₀H₈ClN	详情	详情
(VI)	22394	methyl 4,4-bis[4-(2-quinolinylmethoxy)phenyl]pentanoate		C₃₈H₃₄N₂O₄	详情	详情
(VII)	50960	Methyl levulinate		C₆H₁₀O₃	详情	详情

Extended Information