ethyl (E,4S)-4-[[(2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoyl]amino]-5-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]-2-pentenoate -Drug Synthesis Database

【结构式】

【分子编号】32106

【品名】ethyl (E,4S)-4-[[(2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoyl]amino]-5-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]-2-pentenoate

【CA登记号】

【分子式】C₄₀H₅₄FN₃O₉

【分子量】739.8819832

【元素组成】C 64.93% H 7.36% F 2.57% N 5.68% O 19.46%

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：(XXVII)

Final coupling: Deprotection of (XXVI) with HCl in dioxane followed by condensation with tetrahydrofuranone (XIII) by means of DIEA in DMF gives the amide (XXVII). This compound is also deprotected with HCl as before and condensed with 5-methylisoxazol-3-ylcarbonyl chloride (XVIII) by means of pyridine to afford the protected compound (XXIX), which is finally treated with DDQ, yielding AG-7088.

参考文献中间体

合成目标

【1】 Dragovich, P.S.; Prins, T.J.; Zhou, R.; et al.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements. J Med Chem 1999, 42, 7, 1213.
【2】 Worland, S.T.; Ferre, R.A.; Patick, A.K.; Prins, T.J.; Meador, J.W. III; Zhou, R.; Dragovich, P.S.; Fuhrman, S.A.; Matthews, D.A.; Ford, C.E.; Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. J Med Chem 1999, 42, 7, 1203.
【3】 Graul, A.; Castañer, J.; AG-7088. Drugs Fut 2000, 25, 1, 9.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIII)	32103	tert-butyl (1S)-1-[(2S,4R)-4-(4-fluorobenzyl)-5-oxotetrahydro-2-furanyl]-2-methylpropylcarbamate	C₂₀H₂₈FNO₄	详情	详情
(XXVI)	32105	ethyl (E,4S)-4-[(tert-butoxycarbonyl)amino]-5-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]-2-pentenoate	C₂₅H₃₆N₂O₇	详情	详情
(XXVII)	32106	ethyl (E,4S)-4-[[(2R,5S)-5-[(tert-butoxycarbonyl)amino]-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoyl]amino]-5-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]-2-pentenoate	C₄₀H₅₄FN₃O₉	详情	详情
(XXVIII)	32107	5-methyl-3-isoxazolecarbonyl chloride	C₅H₄ClNO₂	详情	详情
(XXIX)	32108	ethyl (E,4S)-5-[(3S)-1-(2,4-dimethoxybenzyl)-2-oxopyrrolidinyl]-4-[((2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-[[(5-methyl-3-isoxazolyl)carbonyl]amino]-4-oxoheptanoyl)amino]-2-pentenoate	C₄₀H₄₉FN₄O₉	详情	详情

Extended Information