1-(2-amino-2-oxoethyl)-4-[2-[2-([(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]methyl)-1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl]ethyl]-1,4-diazoniabicyclo[2.2.2 -Drug Synthesis Database

【结构式】

【分子编号】30161

【品名】1-(2-amino-2-oxoethyl)-4-[2-[2-([(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]methyl)-1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl]ethyl]-1,4-diazoniabicyclo[2.2.2

【CA登记号】

【分子式】C₃₉H₄₄ClF₃N₆O₁₂S₂

【分子量】945.3915096

【元素组成】C 49.55% H 4.69% Cl 3.75% F 6.03% N 8.89% O 20.31% S 6.78%

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：(L)

Coupling of carbapenem (XLII) with sultam (VIIIb) under Mitsunobu conditions gave adduct (XLVII), which was desylilated to yield alcohol (XLVIII). Formation of the corresponding triflate, followed by condensation with bicyclic compound (XLV) provided (II), which was converted to (L) upon treatment with HCl and NaCl. The p-nitrobenzyl ester of (L) was finally deprotected by hydrogenation over Pd/C to provide the title carboxylic acid. A further procedure to obtain the target compound is to repeat the described synthesis but using carbapenem (XXXVII), instead of carbapenem (XLII).

参考文献中间体

合成目标

【1】 Yasuda, N.; et al.; Preparation of anti-MRS carbapenem L-786,392. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-31.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VIIIb)	30125	6-[2-[(triethylsilyl)oxy]ethyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione	C₁₈H₂₅NO₃SSi	详情	详情
(IL)	30160	1-(2-amino-2-oxoethyl)-4-(2-[2-[((4S,5R,6S)-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-3-yl)methyl]-1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl]ethyl)-1,4-diazonia	C₄₆H₅₈F₆N₆O₁₅S₃Si	详情	详情
(XLII)	30154	(4S,5R,6S)-3-(hydroxymethyl)-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-7-one	C₂₄H₃₄N₂O₇Si	详情	详情
(XLV)	30156	1-(2-amino-2-oxoethyl)-4-aza-1-azoniabicyclo[2.2.2]octane trifluoromethanesulfonate	C₉H₁₆F₃N₃O₄S	详情	详情
(XLVII)	30158	2-[((4S,5R,6S)-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-3-yl)methyl]-6-[2-[(triethylsilyl)oxy]ethyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione	C₄₂H₅₇N₃O₉SSi₂	详情	详情
(XLVIII)	30159	6-(2-hydroxyethyl)-2-[((4S,5R,6S)-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-6-[(1R)-1-[(triethylsilyl)oxy]ethyl]-1-azabicyclo[3.2.0]hept-2-en-3-yl)methyl]-2H-naphtho[1,8-cd]isothiazole-1,1(2H)-dione	C₃₆H₄₃N₃O₉SSi	详情	详情
(L)	30161	1-(2-amino-2-oxoethyl)-4-[2-[2-([(4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-[2-(4-nitrobenzyloxy)acetyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]methyl)-1,1-dioxo-1,2-dihydro-2H-naphtho[1,8-cd]isothiazol-6-yl]ethyl]-1,4-diazoniabicyclo[2.2.2	C₃₉H₄₄ClF₃N₆O₁₂S₂	详情	详情

Extended Information