2,4-dibromobutanoyl chloride -Drug Synthesis Database

【结构式】

【分子编号】20577

【品名】2,4-dibromobutanoyl chloride

【CA登记号】

【分子式】C₄H₅Br₂ClO

【分子量】264.3438

【元素组成】C 18.17% H 1.91% Br 60.45% Cl 13.41% O 6.05%

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：(II)

The reaction of gamma-butyrolactone (I) with Br2 and PBr3 at 100 C followed by a treatment with SOCl2 gives 2,4-dibromobutanoyl chloride (II), which is condensed with O-methylhydroxylamine by means of NaOH in CHCl3 yielding N-methoxy-3-bromopyrrolidin-2-one (III). The reaction of (III) with triphenylphosphine (IV) in hot THF affords the triphenylphosphonium salt (V), which is finally condensed with 3,5-di(tert-butyl)-4-hydroxybenzaldehyde (VI) by means of triethylamine in hot ethanol.

参考文献中间体

合成目标

【1】 Ikuta, H.; Yamagishi, Y.; Akasaka, K.; Yamatsu, I.; Kobayashi, S.; Shirota, H.; Katayamaa, K. (Eisai Co., Ltd.); 2-Pyrrolidone derivatives, process for preparing them, pharmaceutical compositions and use. AU 8656766; EP 0204964; ES 8800148; JP 1986257967; US 4833160 .
【2】 Shirota, H.; Yamatsu, I.; Yamada, K.; Yomagishi, Y.; Katayama, K.; Kobayashi, S.; Ikuta, H.; Synthesis and antiinflammatory activities of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-ones. J Med Chem 1987, 30, 11, 1995.
【3】 Prous, J.; Castaner, J.; E-5110. Drugs Fut 1989, 14, 4, 307.

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)	20576	dihydro-2(3H)-furanone	96-48-0	C₄H₆O₂	详情	详情
(II)	20577	2,4-dibromobutanoyl chloride		C₄H₅Br₂ClO	详情	详情
(III)	20578	3-bromo-1-methoxy-2-pyrrolidinone		C₅H₈BrNO₂	详情	详情
(V)	20579	(1-methoxy-2-oxo-3-pyrrolidinyl)(triphenyl)phosphonium bromide		C₂₃H₂₃BrNO₂P	详情	详情
(VI)	14875	3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde; 3,5-di(tert-butyl)-4-hydroxybenzaldehyde; 3,5-Di-tert-butyl-4-hydroxybenzaldehyde	1620-98-0	C₁₅H₂₂O₂	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 2,4-dibromobutyrylchloride (I) was reacted with N-methylhydroxylamine (II) in methylene chloride with NaOH to yield 4-bromo-2-methyl-5,6-dihydro-2H-1,2-oxazin-3(4H)-one (III). The reaction of (III) and zinc with 3,5-di-tert-butyl-4-hydroxybenzaldehyde (IV) underwent Reformatsky-type reaction. Dehydration of the hydroxymethyl intermediate (V) in refluxing toluene with p-toluenesulfonic acid afforded BF-389.

参考文献中间体

合成目标

【1】 Lee, S.J.; Frierson, M.R. III, Wong, S.; Naismith, R.W.; BF-389. Drugs Fut 1992, 17, 1, 12.

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)	20577	2,4-dibromobutanoyl chloride		C₄H₅Br₂ClO	详情	详情
(II)	12690	(Hydroxyamino)methane; N-Methylhydroxylamine	593-77-1	CH₅NO	详情	详情
(III)	14874	4-bromo-2-methyl-1,2-oxazinan-3-one		C₅H₈BrNO₂	详情	详情
(IV)	14875	3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzaldehyde; 3,5-di(tert-butyl)-4-hydroxybenzaldehyde; 3,5-Di-tert-butyl-4-hydroxybenzaldehyde	1620-98-0	C₁₅H₂₂O₂	详情	详情
(V)	14876	4-[[3,5-di(tert-butyl)-4-hydroxyphenyl](hydroxy)methyl]-2-methyl-1,2-oxazinan-3-one		C₂₀H₃₁NO₄	详情	详情

Extended Information