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【结 构 式】

【分子编号】20579

【品名】(1-methoxy-2-oxo-3-pyrrolidinyl)(triphenyl)phosphonium bromide

【CA登记号】

【 分 子 式 】C23H23BrNO2P

【 分 子 量 】456.318922

【元素组成】C 60.54% H 5.08% Br 17.51% N 3.07% O 7.01% P 6.79%

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:(V)

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.

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
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