benzyl 3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】29408

【品名】benzyl 3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenylcarbamate

【CA登记号】

【分子式】C₁₆H₁₃FN₄O₂

【分子量】312.3033832

【元素组成】C 61.54% H 4.2% F 6.08% N 17.94% O 10.25%

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：(VI)

The reaction between 1,2,3-triazole (I) and 3,4-difluoronitrobenzene (II) afforded a mixture of two regioisomeric substituted triazoles (III) and (IV), from which the required 1-substituted isomer (III) was isolated by column chromatography. Reduction of the nitro group of (III) by hydrogenation over Raney-Ni gave aniline (V), which was converted to carbamate (VI) upon treatment with benzyl chloroformate. Subsequent condensation of (VI) with (R)-(-)-glycidyl butyrate (VII) in the presence of lithium bis(trimethylsilyl)amide produced the chiral oxazolidinone (VIII). Mesylation of the alcohol group of (VIII), followed by displacement with NaN3 yielded azide (IX). This was reduced by hydrogenation over Raney-Ni to give amine (X), which was finally acetylated using Ac2O and pyridine.

参考文献中间体

合成目标

【1】 Emmert, D.E.; Reischer, R.J.; Ford, C.W.; Garmon, S.A.; Zurenko, G.E.; Barbachyn, M.R.; Hutchinson, D.K.; Stelzer, L.S.; Hester, J.B.; Synthesis and antibacterial activity of azolylphenyloxazolidinones having nitrogen-bound five-membered heterocyclic rings. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-137.
【2】 Hutchinson, D.K. (Pharmacia & Upjohn AB); Hetero-aromatic ring substd. phenyloxazolidinone antimicrobials. EP 0807112; JP 1998513446; US 5910504; WO 9623788 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10101	Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene	501-53-1	C₈H₇ClO₂	详情	详情
(I)	29404	1H-1,2,3-triazole	288-36-8	C₂H₃N₃	详情	详情
(II)	17013	1,2-difluoro-4-nitrobenzene; 3,4-Difluoronitrobenzene	369-34-6	C₆H₃F₂NO₂	详情	详情
(III)	29405	1-(2-fluoro-4-nitrophenyl)-1H-1,2,3-triazole		C₈H₅FN₄O₂	详情	详情
(IV)	29406	2-(2-fluoro-4-nitrophenyl)-2H-1,2,3-triazole		C₈H₅FN₄O₂	详情	详情
(V)	29407	3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenylamine3-fluoro-4-(1H-1,2,3-triazol-1-yl)aniline		C₈H₇FN₄	详情	详情
(VI)	29408	benzyl 3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenylcarbamate		C₁₆H₁₃FN₄O₂	详情	详情
(VII)	18385	(2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate	60456-26-0	C₇H₁₂O₃	详情	详情
(VIII)	29409	(5R)-3-[3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one		C₁₂H₁₁FN₄O₃	详情	详情
(IX)	29410	(5R)-5-(azidomethyl)-3-[3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one		C₁₂H₁₀FN₇O₂	详情	详情
(X)	29411	(5S)-5-(aminomethyl)-3-[3-fluoro-4-(1H-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one		C₁₂H₁₂FN₅O₂	详情	详情

Extended Information