【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% |
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 |