7-[(1R,5S)-6-[((2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl)amino]-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】43092

【品名】7-[(1R,5S)-6-[((2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl)amino]-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

【CA登记号】

【分子式】C₂₆H₂₅F₃N₆O₅

【分子量】558.5171496

【元素组成】C 55.91% H 4.51% F 10.2% N 15.05% O 14.32%

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)

Amino acid (XI) was then coupled with N-Boc-L-alanine (XII) using EDC and HOBt to furnish amide (XIII), and its Boc group was subsequently cleaved with HCl in dioxan, yielding (XIV). A second coupling with N-Boc-L-alanine (XII), followed by acid deprotection gave (XV) as the hydrochloride salt. Conversion to the title methanesulfonate salt was carried out by liberation of the base with NaHCO3 and subsequent treatment with MsOH acetone.

参考文献中间体

合成目标

【1】 Brighty, K.E. (Pfizer Inc.); Anti-bacterial azabicyclo quinolone carboxylic acids. US 5229396 .
【2】 Brighty, K.E. (Pfizer Inc.); Azabicyclo quinolone and naphthyridone carboxylic acids. US 5164402 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	43089	7-[(1R,5S)-6-amino-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid		C₂₀H₁₅F₃N₄O₃	详情	详情
(XII)	26450	Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid	15761-38-3	C₈H₁₅NO₄	详情	详情
(XIII)	43090	7-[(1R,5S)-6-([(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid		C₂₈H₂₈F₃N₅O₆	详情	详情
(XIV)	43091	7-((1R,5S)-6-[[(2S)-2-aminopropanoyl]amino]-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid		C₂₃H₂₀F₃N₅O₄	详情	详情
(XV)	43092	7-[(1R,5S)-6-[((2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl)amino]-3-azabicyclo[3.1.0]hex-3-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid		C₂₆H₂₅F₃N₆O₅	详情	详情

Extended Information