benzyl 2-(acetoxy)-3-(2-ethoxy-2-oxoethyl)-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】43309

【品名】benzyl 2-(acetoxy)-3-(2-ethoxy-2-oxoethyl)-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate

【CA登记号】

【分子式】C₂₁H₂₆N₂O₇

【分子量】418.44672

【元素组成】C 60.28% H 6.26% N 6.69% O 26.76%

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：(XXIV)

The synthesis of the intermediate carboxylic acid (XV) has been reported by an alternative procedure. The cyclic anhydride (III) was condensed with glycine ethyl ester (XXI) in refluxing Ac2O, yielding the cyclic imide (XXII). Reduction of the imide (XXII) with NaBH4 produced the aminal (XXIII), which was subsequently converted to the more reactive acetoxyamide (XXIV). Boron trifluoride-catalyzed addition of propargyl trimethylsilane (XXV) to the acetoxyamide (XXIV) gave rise to allene (XXVI). This underwent smooth ozonolysis to the aldehyde (XXVII). After protection of the aldehyde (XXVII) as the dimethyl acetal (XIV), hydrolysis of the ethyl ester group gave the intermediate carboxylic acid (XV).

参考文献中间体

合成目标

【1】 Reich, S.; Guo, C.X.; Villafranca, E.; Showalter, R.; Dong, L.; A concise synthesis of AG5473/5507 utilizing N-acyliminium ion chemistry. Tetrahedron Lett 2000, 41, 28, 5307.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	43292	benzyl 2,4-dioxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate		C₁₅H₁₅NO₅	详情	详情
(XIV)	43302	benzyl 2-(dimethoxymethyl)-3-(2-ethoxy-2-oxoethyl)-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₂H₃₀N₂O₇	详情	详情
(XV)	43303	2-[9-[(benzyloxy)carbonyl]-2-(dimethoxymethyl)-4-oxo-3,9-diazabicyclo[3.3.1]non-3-yl]acetic acid		C₂₀H₂₆N₂O₇	详情	详情
(XXI)	10309	ethyl 2-aminoacetate; Glycine ethyl ester	459-73-4	C₄H₉NO₂	详情	详情
(XXII)	43307	benzyl 3-(2-ethoxy-2-oxoethyl)-2,4-dioxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₁₉H₂₂N₂O₆	详情	详情
(XXIII)	43308	benzyl 3-(2-ethoxy-2-oxoethyl)-2-hydroxy-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₁₉H₂₄N₂O₆	详情	详情
(XXIV)	43309	benzyl 2-(acetoxy)-3-(2-ethoxy-2-oxoethyl)-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₁H₂₆N₂O₇	详情	详情
(XXV)	43310	trimethyl(2-propynyl)silane	13361-64-3	C₆H₁₂Si	详情	详情
(XXVI)	43311	benzyl 3-(2-ethoxy-2-oxoethyl)-2-oxo-4-(1,2-propadienyl)-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₂H₂₆N₂O₅	详情	详情
(XXVII)	43312	benzyl 3-(2-ethoxy-2-oxoethyl)-2-formyl-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₀H₂₄N₂O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXIV)

参考文献中间体

合成目标

【1】 Reich, S.; Guo, C.X.; Villafranca, E.; Showalter, R.; Dong, L.; A concise synthesis of AG5473/5507 utilizing N-acyliminium ion chemistry. Tetrahedron Lett 2000, 41, 28, 5307.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	43292	benzyl 2,4-dioxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate		C₁₅H₁₅NO₅	详情	详情
(XIV)	43302	benzyl 2-(dimethoxymethyl)-3-(2-ethoxy-2-oxoethyl)-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₂H₃₀N₂O₇	详情	详情
(XV)	43303	2-[9-[(benzyloxy)carbonyl]-2-(dimethoxymethyl)-4-oxo-3,9-diazabicyclo[3.3.1]non-3-yl]acetic acid		C₂₀H₂₆N₂O₇	详情	详情
(XXI)	10309	ethyl 2-aminoacetate; Glycine ethyl ester	459-73-4	C₄H₉NO₂	详情	详情
(XXII)	43307	benzyl 3-(2-ethoxy-2-oxoethyl)-2,4-dioxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₁₉H₂₂N₂O₆	详情	详情
(XXIII)	43308	benzyl 3-(2-ethoxy-2-oxoethyl)-2-hydroxy-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₁₉H₂₄N₂O₆	详情	详情
(XXIV)	43309	benzyl 2-(acetoxy)-3-(2-ethoxy-2-oxoethyl)-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₁H₂₆N₂O₇	详情	详情
(XXV)	43310	trimethyl(2-propynyl)silane	13361-64-3	C₆H₁₂Si	详情	详情
(XXVI)	43311	benzyl 3-(2-ethoxy-2-oxoethyl)-2-oxo-4-(1,2-propadienyl)-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₂H₂₆N₂O₅	详情	详情
(XXVII)	43312	benzyl 3-(2-ethoxy-2-oxoethyl)-2-formyl-4-oxo-3,9-diazabicyclo[3.3.1]nonane-9-carboxylate		C₂₀H₂₄N₂O₆	详情	详情

Extended Information