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【结 构 式】

【分子编号】62253

【品名】1-[3-fluoro-4-(3-oxetanyl)phenyl]-2,5-dimethyl-1H-pyrrole

【CA登记号】

【 分 子 式 】C15H16FNO

【 分 子 量 】245.2965832

【元素组成】C 73.45% H 6.57% F 7.75% N 5.71% O 6.52%

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:(VII)

Condensation of 2-fluoro-4-nitrotoluene (I) with paraformaldehyde under basic conditions affords diol (II). Nitro group reduction in (II) by hydrogenation over Pd/C yields aniline (III), which is further protected with acetylacetone (IV), to produce the pyrrole derivative (V). After conversion of diol (V) into the mono-tosylate (VI), cyclization in the presence of BuLi furnishes the oxetane derivative (VII). Removal of the pyrrole moiety of (VII) by treatment with hydroxylamine provides amine (VIII), which is converted to the carbamate (IX) by acylation with benzyl chloroformate. Finally, condensation of (IX) with (S)-N,O-diacetyl-1-amino-3-chloro-2-propanol (X) in the presence of lithium t-butoxide produces the required oxazolidinone derivative.

1 Hao, Y.; Barbachyn, M.R.; Greene, M.L.; et al.; Synthesis and antibacterial activities of oxazolidinones incorporating C-ring oxetanes and thietanes. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1321.
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) 55902 2-Fluoro-4-nitrotoluene; 4-Nitro-2-fluorotoluene 1427-07-2 C7H6FNO2 详情 详情
(II) 62249 2-(2-fluoro-4-nitrophenyl)-1,3-propanediol C9H10FNO4 详情 详情
(III) 62250 2-(4-amino-2-fluorophenyl)-1,3-propanediol C9H12FNO2 详情 详情
(IV) 11620 2,4-Pentanedione;acetylacetone 123-54-6 C5H8O2 详情 详情
(V) 62251 2-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-fluorophenyl]-1,3-propanediol C15H18FNO2 详情 详情
(VI) 62252 2-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-fluorophenyl]-3-hydroxypropyl 4-methylbenzenesulfonate C22H24FNO4S 详情 详情
(VII) 62253 1-[3-fluoro-4-(3-oxetanyl)phenyl]-2,5-dimethyl-1H-pyrrole C15H16FNO 详情 详情
(VIII) 62254 3-fluoro-4-(3-oxetanyl)aniline; 3-fluoro-4-(3-oxetanyl)phenylamine C9H10FNO 详情 详情
(IX) 62255 benzyl 3-fluoro-4-(3-oxetanyl)phenylcarbamate C17H16FNO3 详情 详情
(X) 61915 (1S)-2-(acetylamino)-1-(chloromethyl)ethyl acetate C7H12ClNO3 详情 详情
Extended Information