(5R)-5-(azidomethyl)-3-phenyl-1,3-oxazolidin-2-one -Drug Synthesis Database

【结构式】

【分子编号】61917

【品名】(5R)-5-(azidomethyl)-3-phenyl-1,3-oxazolidin-2-one

【CA登记号】

【分子式】C₁₀H₁₀N₄O₂

【分子量】218.21516

【元素组成】C 55.04% H 4.62% N 25.68% O 14.66%

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：(I)

The reaction of 5(R)-(azidomethyl)-3-phenyloxazolidin-2-one (I) with Ac2O and MsOH gives the 4-acetylphenyl derivative (II), which is cyclized with glyoxylic acid (III) and hydrazine (IV) in hot acetic acid to yield the pyridazinone derivative (V). The reduction of the azido group of (V) by means of PPh3 in THF/water affords the aminomethyl compound (VI), which is finally condensed with ethyl dithioacetate (VII) by means of TEA in DMF to provide the target thioacetamide.

参考文献中间体

合成目标

【1】 Luehr, G.W.; Wang, S.; Hackbarth, C.J.; Gomez, M.; Trias, J.; Patel, D.V.; Gordeev, M.F.; Novel antimicrobial pyridazine phenyloxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1320.

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)	61917	(5R)-5-(azidomethyl)-3-phenyl-1,3-oxazolidin-2-one		C₁₀H₁₀N₄O₂	详情	详情
(II)	61918	(5R)-3-(4-acetylphenyl)-5-(azidomethyl)-1,3-oxazolidin-2-one		C₁₂H₁₂N₄O₃	详情	详情
(III)	15618	2-Oxoacetic acid; Glyoxylic Acid	298-12-4	C₂H₂O₃	详情	详情
(IV)	27344	hydrazine	302-01-2	H₄N₂	详情	详情
(V)	61919	6-{4-[(5R)-5-(azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3(2H)-pyridazinone		C₁₄H₁₂N₆O₃	详情	详情
(VI)	61920	6-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3(2H)-pyridazinone		C₁₄H₁₄N₄O₃	详情	详情
(VII)	61921	propyl ethanedithioate		C₅H₁₀S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The reaction of 5(R)-(azidomethyl)-3-phenyloxazolidin-2-one (I) with Ac2O and MsOH gives the 4-acetylphenyl derivative (II), which is cyclized with glyoxylic acid (III) and hydrazine (IV) in hot acetic acid to yield the pyridazinone derivative (V). The reduction of the azido group of (V) by means of PPh3 in THF/water affords the aminomethyl compound (VI), which is condensed with acetic anhydride and pyridine to provide the acetamide (VII). Finally, this compound is treated with Lawesson's reagent in hot dioxane to furnish the target pyridazinethione.

参考文献中间体

合成目标

【1】 Luehr, G.W.; Wang, S.; Hackbarth, C.J.; Gomez, M.; Trias, J.; Patel, D.V.; Gordeev, M.F.; Novel antimicrobial pyridazine phenyloxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1320.

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)	61917	(5R)-5-(azidomethyl)-3-phenyl-1,3-oxazolidin-2-one		C₁₀H₁₀N₄O₂	详情	详情
(II)	61918	(5R)-3-(4-acetylphenyl)-5-(azidomethyl)-1,3-oxazolidin-2-one		C₁₂H₁₂N₄O₃	详情	详情
(III)	15618	2-Oxoacetic acid; Glyoxylic Acid	298-12-4	C₂H₂O₃	详情	详情
(IV)	27344	hydrazine	302-01-2	H₄N₂	详情	详情
(V)	61919	6-{4-[(5R)-5-(azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3(2H)-pyridazinone		C₁₄H₁₂N₆O₃	详情	详情
(VI)	61920	6-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3(2H)-pyridazinone		C₁₄H₁₄N₄O₃	详情	详情
(VII)	61922	N-({(5S)-2-oxo-3-[4-(6-oxo-1,6-dihydro-3-pyridazinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide		C₁₆H₁₆N₄O₄	详情	详情

Extended Information