tert-butyl (2R,3S,5R)-5-cyano-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)methyl]-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】55171

【品名】tert-butyl (2R,3S,5R)-5-cyano-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)methyl]-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₉H₃₀N₂O₅

【分子量】366.45768

【元素组成】C 62.27% H 8.25% N 7.64% O 21.83%

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：(XXVIII)

In an alternative synthesis, copper-catalyzed conjugate addition of propenylmagnesium bromide to the chiral pyrrolidone (XXIV) afforded the propenyl pyrrolidinone (XXV). Reduction of the lactam function of (XXV) by means of DIBAL gave the 2-ydroxypyrrolidine (XXVI), which was reacted with trimethylsilyl cyanide and boron trifluoride to provide nitrile (XXVII). Alcohol (XXVIII), obtained by desilylation of (XXVII) with tetrabutylammonium fluoride, was converted to azide (XXIX) upon treatment with DPPA under Mitsunobu conditions. Azide (XXIX) was then reduced to the primary amine (XXX), employing triphenylphosphine in moist THF. Subsequent acylation with Ac2O furnished acetamide (XXXI).

参考文献中间体

合成目标

【1】 Inhibitors of neuraminidases. WO 0128996 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXIV)	55167	tert-butyl (2R)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate	C₂₁H₃₇NO₆Si	详情	详情
(XXV)	55168	tert-butyl (2R,3S)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-oxo-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate	C₂₄H₄₃NO₆Si	详情	详情
(XXVI)	55169	tert-butyl (2R,3S)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-hydroxy-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate	C₂₄H₄₅NO₆Si	详情	详情
(XXVII)	55170	tert-butyl (2R,3S,5R)-2-{(S)-{[tert-butyl(dimethyl)silyl]oxy}[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate	C₂₅H₄₄N₂O₅Si	详情	详情
(XXVIII)	55171	tert-butyl (2R,3S,5R)-5-cyano-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)methyl]-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate	C₁₉H₃₀N₂O₅	详情	详情
(XXIX)	55172	tert-butyl (2R,3S,5R)-2-{(R)-azido[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate	C₁₉H₂₉N₅O₄	详情	详情
(XXX)	55173	tert-butyl (2R,3S,5R)-2-{(R)-amino[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-5-cyano-3-[(Z)-1-propenyl]-1-pyrrolidinecarboxylate	C₁₉H₃₁N₃O₄	详情	详情

Extended Information