(2S)-2-aminobutyric acid -Drug Synthesis Database

【结构式】

【分子编号】32037

【品名】(2S)-2-aminobutyric acid

【CA登记号】1492-24-6

【分子式】C₄H₉NO₂

【分子量】103.121

【元素组成】C 46.59% H 8.8% N 13.58% O 31.03%

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)

The reaction of 2(S)-aminobutyric acid (I) with SOCl2 gives the acyl chloride (II), which is treated with methanol to yield the methyl ester (III). The condensation of (III) with ethyl 4-bromobutyrate (IV) by means of Na2CO3 in refluxing water affords 2(S)-[3-(ethoxycarbonyl)propylamino)butyric acid methyl ester (V), which is cyclized by means of 2-pyridinol in refluxing toluene to provide 2(S)-(2-oxopyrrolidin-1-yl)butyric acid methyl ester (VI). Finally this compound is treated with ammonia in water to furnish the target Lavetiracetam.

参考文献中间体

合成目标

【1】 Cavoy, E.; Ates, C.; Surtees, J.; Burteau, A.-C.; Marmon, V. (UCB SA); Oxopyrrolidine cpds., preparation of said cpds. and their use in the manufacturing of levetiracetam and analogues. WO 0314080 .

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)	32037	(2S)-2-aminobutyric acid	1492-24-6	C₄H₉NO₂	详情	详情
(II)	61972	(2S)-2-aminobutanoyl chloride		C₄H₈ClNO	详情	详情
(III)	61973	methyl (2S)-2-aminobutanoate		C₅H₁₁NO₂	详情	详情
(IV)	61974	Ethyl 4-bromobutyrate; 4-Bromobutyric acid ethyl ester; Ethyl g-Bromobutyrate; Ethyl-(4-brombutyrat); 4-Bromo-n-butyric Acid Ethyl Ester; Ethyl 4-Bromo-n-butyrate; 4-Bromobutyric acid ethylester; Ethylbromobutyrate; 4-Bromobutyric Acid, Ethyl Ester; Ethyl-4-bromobutyrate; 4-BBE	2969-81-5	C₆H₁₁BrO₂	详情	详情
(V)	61975	methyl (2S)-2-[(4-ethoxy-4-oxobutyl)amino]butanoate		C₁₁H₂₁NO₄	详情	详情
(VI)	61971	methyl (2S)-2-(2-oxo-1-pyrrolidinyl)butanoate		C₉H₁₅NO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The condensation of 2,4-difluoronitrobenzene (I) with 2(S)-aminobutyric acid (II) by means of triethylamine in refluxing acetone gives 2(S)-(5-fluoro-2-nitrophenylamino)butyric acid (III), which is reductocyclized with H2 over Raney-Ni in methanol/acetic acid, yielding 3(S)-ethyl-6-fluoro-1,2,3,4-tetrahydroquinoxalin-2-one (IV). Finally, this compound is treated with isopropyl chloroformate (V) and 4-methylpyridine in dichloromethane.

参考文献中间体

合成目标

【1】 Rosner, M.; Billhardt-Troughton, U.-M.; Kirsch, R.; Kleim, J.-P.; Meichsner, C.; Riess, G.; Winkler, I. (Aventis SA); Quinoxalines, process for their preparation, and their use. CA 2160859; DE 4437406; EP 0708093; JP 1996225544; US 5723461 .
【2】 Graul, A.; Castañer, J.; Rabasseda, X.; GW-420867X. Drugs Fut 2000, 25, 1, 24.

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)	32036	2,4-difluoro-1-nitrobenzene	446-35-5	C₆H₃F₂NO₂	详情	详情
(II)	32037	(2S)-2-aminobutyric acid	1492-24-6	C₄H₉NO₂	详情	详情
(III)	32038	(2S)-2-(5-fluoro-2-nitroanilino)butyric acid		C₁₀H₁₁FN₂O₄	详情	详情
(IV)	32039	(3S)-3-ethyl-6-fluoro-3,4-dihydro-2(1H)-quinoxalinone		C₁₀H₁₁FN₂O	详情	详情
(V)	26492	2-[(chlorocarbonyl)oxy]propane	108-23-6	C₄H₇ClO₂	详情	详情

Extended Information