【结 构 式】 |
【分子编号】62790 【品名】(5S)-3-(4-acetyl-3-fluorophenyl)-5-(aminomethyl)-1,3-oxazolidin-2-one 【CA登记号】 |
【 分 子 式 】C12H13FN2O3 【 分 子 量 】252.2453032 【元素组成】C 57.14% H 5.19% F 7.53% N 11.11% O 19.03% |
合成路线1
该中间体在本合成路线中的序号:(VIII)3-Fluoroaniline (I) is condensed with benzyl chloroformate to give carbamate (II). Reaction of (II) with (R)-glycidol butyrate (III) in the presence of butyllithium affords oxazolidinone (IV). After conversion of alcohol (IV) to the corresponding mesylate, displacement with NaN3 provides azide (V). Reduction and acylation of (V) by means of thioacetic acid leads to acetamide (VI). Friedel-Crafts acylation of the aromatic ring of (VI) with acetic anhydride in the presence of methanesulfonic acid furnishes acetophenone (VII). Acidic hydrolysis of acetamide (VII) yields amine (VIII). This is then treated with thiophosgene, followed by methanol, to produce the thiocarbamate (IX). Finally, aldol condensation of the acetophenone (IX) with pyridine-2-carbaldehyde (X) gives rise to the target compound.
【1】 Selvakumar, N.; et al.; Synthesis and antibacterial activity of novel chalcone oxazolidinone hybrids. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1323. |
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) | 20697 | 3-fluoroaniline; 3-fluorophenylamine | 372-19-0 | C6H6FN | 详情 | 详情 |
(II) | 60314 | phenylmethyl 3-fluorophenylcarbamate | C14H12FNO2 | 详情 | 详情 | |
(III) | 18385 | (2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate | 60456-26-0 | C7H12O3 | 详情 | 详情 |
(IV) | 60315 | 3-(3-fluorophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one | C10H10FNO3 | 详情 | 详情 | |
(V) | 60317 | (R)-5-(azidomethyl)-3-(3-fluorophenyl)oxazolidin-2-one | C10H9FN4O2 | 详情 | 详情 | |
(VI) | 60319 | N-{[3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide | C12H13FN2O3 | 详情 | 详情 | |
(VII) | 62789 | N-{[(5S)-3-(4-acetyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide | C14H15FN2O4 | 详情 | 详情 | |
(VIII) | 62790 | (5S)-3-(4-acetyl-3-fluorophenyl)-5-(aminomethyl)-1,3-oxazolidin-2-one | C12H13FN2O3 | 详情 | 详情 | |
(IX) | 62791 | O-methyl [(5S)-3-(4-acetyl-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methylcarbamothioate | C14H15FN2O4S | 详情 | 详情 | |
(X) | 25173 | 2-pyridinecarbaldehyde | 1121-60-4 | C6H5NO | 详情 | 详情 |