N-[1-(1-[(3,4-difluorophenyl)methyl]-2-{[1-formyl-2-(2-oxo-3-pyrrolidinyl)ethyl]amino}-2-oxoethyl)-2-oxo-1,2-dihydro-3-pyridinyl]-5-methyl-3-isoxazolecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】63737

【品名】N-[1-(1-[(3,4-difluorophenyl)methyl]-2-{[1-formyl-2-(2-oxo-3-pyrrolidinyl)ethyl]amino}-2-oxoethyl)-2-oxo-1,2-dihydro-3-pyridinyl]-5-methyl-3-isoxazolecarboxamide

【CA登记号】

【分子式】C₂₆H₂₅F₂N₅O₆

【分子量】541.5114064

【元素组成】C 57.67% H 4.65% F 7.02% N 12.93% O 17.73%

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：(XV)

Treatment of the Boc-protected aminoalcohol (XII) with trifluoroacetic acid furnishes (XIII). This is then coupled with acid (XI) in the presence of HATU to afford the amide alcohol (XIV). Oxidation of (XIV) with the Dess-Martin periodinane (DMP) reagent gives rise to aldehyde (XV). Finally, Wittig condensation of aldehyde (XV) with isopropoxycarbonylmethylene triphenylphosphorane provides the target unsaturated ester. (1,2)

参考文献中间体

合成目标

【1】 Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors: 6. Structure-activity studies of orally bioavailable, 2-pyridone-containing peptidomimetics. J Med Chem 2002, 45, 8, 1607.
【2】 Dragovich, P.S.; Prins, T.J.; Zhou, R.; Johnson, T.O. Jr. (Agouron Pharmaceuticals, Inc.); Antipicornaviral cpds. and compsns., their pharmaceutical uses, and material for their synthesis. JP 2003515591; US 2001047006; US 6514997; WO 0140189 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XI)	63734	3-(3,4-difluorophenyl)-2-[3-{[(5-methyl-3-isoxazolyl)carbonyl]amino}-2-oxo-1(2H)-pyridinyl]propanoic acid	C₁₉H₁₅F₂N₃O₅	详情	详情
(XII)	55039	tert-butyl (1S)-2-hydroxy-1-{[(3S)-2-oxopyrrolidinyl]methyl}ethylcarbamate	C₁₂H₂₂N₂O₄	详情	详情
(XIII)	63735	3-(2-amino-3-hydroxypropyl)-2-pyrrolidinone	C₇H₁₄N₂O₂	详情	详情
(XIV)	63736	N-{1-[1-[(3,4-difluorophenyl)methyl]-2-({2-hydroxy-1-[(2-oxo-3-pyrrolidinyl)methyl]ethyl}amino)-2-oxoethyl]-2-oxo-1,2-dihydro-3-pyridinyl}-5-methyl-3-isoxazolecarboxamide	C₂₆H₂₇F₂N₅O₆	详情	详情
(XV)	63737	N-[1-(1-[(3,4-difluorophenyl)methyl]-2-{[1-formyl-2-(2-oxo-3-pyrrolidinyl)ethyl]amino}-2-oxoethyl)-2-oxo-1,2-dihydro-3-pyridinyl]-5-methyl-3-isoxazolecarboxamide	C₂₆H₂₅F₂N₅O₆	详情	详情

Extended Information