(2S,3S)-3-(ethoxycarbonyl)-2-oxiranecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】24344

【品名】(2S,3S)-3-(ethoxycarbonyl)-2-oxiranecarboxylic acid

【CA登记号】

【分子式】C₆H₈O₅

【分子量】160.12652

【元素组成】C 45.01% H 5.04% O 49.96%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(V)

The condensation of N-(tert-butoxycarbonyl)-L-leucine (I) with 1-2,3,4-trimethoxybenzyl)piperazine (II) by means of N-hydroxysuccinimide (HSI) and dicyclohexylcarbodiimide (DCC) in dichloromethane gives the corresponding acylated piperazine (III), which is deprotected with dry HCl in ethyl acetate yielding the leucine derivative (IV). Finally, this compound is condensed with trans-epoxysuccinic acid monoethyl ester (V) by means of DCC and HSI as before and treated with H2SO4.

参考文献中间体

合成目标

【1】 Hoefke, W.; et al. (Boehringer Ingelheim GmbH); 1-Aryloxy-2-hydroxy-3-[(benzimidazolin-one-substituted alkyl)-amino]-propanes and salts thereof. DE 2644833 .
【2】 Prous, J.; Castaner, J.; NCO-700. Drugs Fut 1986, 11, 11, 941.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	24353	(2S)-2-[[(2,2-dimethylpropanoyl)oxy]amino]-4-methylpentanoic acid	C₁₁H₂₁NO₄	详情	详情
(II)	24354	2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether	C₁₄H₂₂N₂O₃	详情	详情
(III)	24355	(2S)-2-[[(2,2-dimethylpropanoyl)oxy]amino]-4-methyl-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-pentanone	C₂₅H₄₁N₃O₆	详情	详情
(IV)	24356	(2S)-2-amino-4-methyl-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-pentanone	C₂₀H₃₃N₃O₄	详情	详情
(V)	24344	(2S,3S)-3-(ethoxycarbonyl)-2-oxiranecarboxylic acid	C₆H₈O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The estrification of L-trans-epoxysuccinic acid hemi-ethyl ester (I) with 4-nitrophenol (II) by means of dicyclohexylcarbodiimide (DCC) gives the corresponding p-nitrophenyl ester (III), which is then condensed with N-isoamyl L-leucinamide (IV).

参考文献中间体

合成目标

【1】 Soda, K.; et al. (Taisho Pharmaceutical Co., Ltd.); Trans-epoxysuccinic acid derivative. JP 60174777 .
【2】 Castaner, J.; Prous, J.; EST. Drugs Fut 1986, 11, 11, 927.

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)	24344	(2S,3S)-3-(ethoxycarbonyl)-2-oxiranecarboxylic acid		C₆H₈O₅	详情	详情
(II)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(III)	24346	2-ethyl 3-(4-nitrophenyl) (2S,3S)-2,3-oxiranedicarboxylate		C₁₂H₁₁NO₇	详情	详情
(IV)	24347	2-amino-N-isopentyl-4-methylpentanamide		C₁₁H₂₄N₂O	详情	详情

合成路线3

该中间体在本合成路线中的序号：(V)

The synthesis of [14 C]-EST has been described ac cording to the following procedure: The oxidation of fumaric acid (I) with H2O2 gives trans-epoxysuccinic acid (II), which is submitted to optical resolution by means of its salt with L-arginine. The L-trans isomer (III) is esterified with ethanol and H2SO4 to the corresponding diethyl ester (IV), which is hydrolyzed selectively with KOH, affording the monoethyl ester (V). Finally, this monoester 5 condensed with N-isoamyl-L-leucinamide (VI).

参考文献中间体

合成目标

【1】 Fukushima, K.; et al.; In vivo actions of EST (reort 1) - Absorption and excretion of 14C-EST. Kiso To Rinsho 1986, 20, 4, 319.
【2】 Castaner, J.; Prous, J.; EST. Drugs Fut 1986, 11, 11, 927.

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)	23808	Fumaric acid; (E)-2-butenedioic acid	110-17-8	C₄H₄O₄	详情	详情
(II)	24349	2,3-oxiranedicarboxylic acid; Oxirane-2,3-dicarboxylic acid; Epoxysuccinic acid		C₄H₄O₅	详情	详情
(III)	24350	(2S,3S)-2,3-oxiranedicarboxylic acid		C₄H₄O₅	详情	详情
(IV)	24351	diethyl (2S,3S)-2,3-oxiranedicarboxylate	74243-85-9	C₈H₁₂O₅	详情	详情
(V)	24344	(2S,3S)-3-(ethoxycarbonyl)-2-oxiranecarboxylic acid		C₆H₈O₅	详情	详情
(VI)	24347	2-amino-N-isopentyl-4-methylpentanamide		C₁₁H₂₄N₂O	详情	详情

Extended Information