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【结 构 式】

【分子编号】29416

【品名】(5R)-5-(azidomethyl)-3-[3-fluoro-4-(1H-pyrrol-1-yl)phenyl]-1,3-oxazolidin-2-one

【CA登记号】

【 分 子 式 】C14H12FN5O2

【 分 子 量 】301.2801832

【元素组成】C 55.81% H 4.01% F 6.31% N 23.25% O 10.62%

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:(VIII)

The reaction between pyrrole (I) and 3,4-difluoronitrobenzene (II) afforded the N-aryl pyrrole (III). Selective reduction of the nitro group of (III) by hydrogenation over sulfided platinum on carbon gave aniline (IV), which was converted to carbamate (V) upon treatment with benzyl chloroformate. Subsequent condensation of (V) with (R)-(-)-glycidyl butyrate (VI) in the presence of lithium bis(trimethylsilyl)amide produced the chiral oxazolidinone (VII). Mesylation of the alcohol group of (VII), followed by displacement with NaN3 yielded azide (VIII). This was reduced by hydrogenation over Pt/C/S to give amine (IX), which was finally acetylated using Ac2O and pyridine.

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) 21674 1H-pyrrole 109-97-7 C4H5N 详情 详情
(II) 17013 1,2-difluoro-4-nitrobenzene; 3,4-Difluoronitrobenzene 369-34-6 C6H3F2NO2 详情 详情
(III) 29412 1-(2-fluoro-4-nitrophenyl)-1H-pyrrole C10H7FN2O2 详情 详情
(IV) 29413 3-fluoro-4-(1H-pyrrol-1-yl)phenylamine3-fluoro-4-(1H-pyrrol-1-yl)aniline C10H9FN2 详情 详情
(V) 29414 benzyl 3-fluoro-4-(1H-pyrrol-1-yl)phenylcarbamate C18H15FN2O2 详情 详情
(VI) 18385 (2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate 60456-26-0 C7H12O3 详情 详情
(VII) 29415 (5R)-3-[3-fluoro-4-(1H-pyrrol-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one C14H13FN2O3 详情 详情
(VIII) 29416 (5R)-5-(azidomethyl)-3-[3-fluoro-4-(1H-pyrrol-1-yl)phenyl]-1,3-oxazolidin-2-one C14H12FN5O2 详情 详情
(IX) 29417 (5S)-5-(aminomethyl)-3-[3-fluoro-4-(1H-pyrrol-1-yl)phenyl]-1,3-oxazolidin-2-one C14H14FN3O2 详情 详情
Extended Information