1-[[(4-nitrophenoxy)carbonyl]oxy]ethyl acetate -Drug Synthesis Database

【结构式】

【分子编号】50378

【品名】1-[[(4-nitrophenoxy)carbonyl]oxy]ethyl acetate

【CA登记号】

【分子式】C₁₁H₁₁NO₇

【分子量】269.21088

【元素组成】C 49.08% H 4.12% N 5.2% O 41.6%

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：(III)

Alternatively, the conversion of compound (VII) into bosentan can also be performed by reaction of compound (VII) with ethylene glycol mono tert-butyl ether (IX) by means of NaOH in toluene, yielding the tert-butyl ether derivative (X), which is then treated with formic acid at 85-90 C in toluene to give the 2-(formyloxy)ethoxy derivative (XI). Finally, the formyl group is removed by treatment of (XI) with NaOH in H2O.

参考文献中间体

合成目标

【1】 Bayes, M.; Silvestre, J.S.; Sorbera, L.A.; Castaner, J.; Melagatran and Ximelagatran. Drugs Fut 2001, 26, 12, 1155.
【2】 Antonsson, T.; Gustafsson, D.; Hoffmann, K.-J.; Nystrom, J.-E.; Sorensen, H.; Sellen, M. (AstraZeneca plc); Prodrugs of thrombin inhibitors. EP 0995755; JP 2000504313; JP 2001089498; US 5965692; US 6262028; WO 9723499 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	50376	benzyl [4-([[((2S)-1-[(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl]azetidinyl)carbonyl]amino]methyl)phenyl](imino)methylcarbamate	C₃₃H₄₃N₅O₆	详情	详情
(II)	50377	tert-butyl (1R)-2-[(2S)-2-[([4-[amino(imino)methyl]benzyl]amino)carbonyl]azetidinyl]-1-cyclohexyl-2-oxoethylcarbamate	C₂₅H₃₇N₅O₄	详情	详情
(III)	50378	1-[[(4-nitrophenoxy)carbonyl]oxy]ethyl acetate	C₁₁H₁₁NO₇	详情	详情
(IV)	50379	1-[([[[4-([[((2S)-1-[(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl]azetidinyl)carbonyl]amino]methyl)phenyl](imino)methyl]amino]carbonyl)oxy]ethyl acetate	C₃₀H₄₃N₅O₈	详情	详情
(V)	50380	1-[([[(4-[[([(2S)-1-[(2R)-2-amino-2-cyclohexylethanoyl]azetidinyl]carbonyl)amino]methyl]phenyl)(imino)methyl]amino]carbonyl)oxy]ethyl acetate	C₂₅H₃₅N₅O₆	详情	详情
(VI)	50381	ethyl 2-[[(trifluoromethyl)sulfonyl]oxy]acetate	C₅H₇F₃O₅S	详情	详情
(VII)	50382	ethyl 2-[((1R)-2-[(2S)-2-[([4-[([[1-(acetoxy)ethoxy]carbonyl]amino)(imino)methyl]benzyl]amino)carbonyl]azetidinyl]-1-cyclohexyl-2-oxoethyl)amino]acetate	C₂₉H₄₁N₅O₈	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Treatment of p-nitrophenol (I) with 1-chloroethyl chloroformate (II) in the presence of pyridine afforded carbonate (III). Subsequent displacement of the chlorine atom of (III) with mercuric acetate in HOAc provided the acetoxy derivative (IV). This was then condensed with (R)-alpha-methylhistamine (V) in HMPT to furnish the title compound.

参考文献中间体

合成目标

【1】 Stark, H.; et al.; Enzyme-catalyzed prodrug approaches for the histamine H3-receptor agonist (R)-alpha-methylhistamine. Bioorg Med Chem 2001, 9, 1, 191.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	11236	4-Nitrophenol; p-Nitrophenol	100-02-7	C₆H₅NO₃	详情	详情
(II)	22014	1-chloro-1-[(chlorocarbonyl)oxy]ethane	50893-53-3	C₃H₄Cl₂O₂	详情	详情
(III)	51393	1-chloroethyl 4-nitrophenyl carbonate		C₉H₈ClNO₅	详情	详情
(IV)	50378	1-[[(4-nitrophenoxy)carbonyl]oxy]ethyl acetate		C₁₁H₁₁NO₇	详情	详情
(V)	51394	(2R)-1-(1H-imidazol-4-yl)-2-propanamine; (1R)-2-(1H-imidazol-4-yl)-1-methylethylamine		C₆H₁₁N₃	详情	详情

Extended Information