【结 构 式】 |
【分子编号】62753 【品名】N-({(5S)-3-[3,5-difluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide 【CA登记号】 |
【 分 子 式 】C16H19F2N3O3S 【 分 子 量 】371.4080864 【元素组成】C 51.74% H 5.16% F 10.23% N 11.31% O 12.92% S 8.63% |
合成路线1
该中间体在本合成路线中的序号:(VII)Two synthetic methods have been reported for the title compound. Coupling of aryl triflate (I) with thiomorpholine (II) affords the N-aryl thiomorpholine (III). Reduction of the nitroaryl group of (III) by catalytic hydrogenation in the presence of Raney nickel furnishes aniline (IV). This is then condensed with benzyl chloroformate under Schotten-Baumann conditions, yielding carbamate (V). Reaction of carbamate (V) with (S)-N-(2-acetoxy-3-chloropropyl)acetamide (VI) in the presence of lithium tert-butoxide and MeOH leads to the (S)-oxazolidine (VII). Finally, oxidation of the thiomorpholine sulfide group of (VII) with N-methylmorpholine-N-oxide in the presence of a catalytic amount of OsO4 gives rise to the title sulfone compound.
【1】 Greene, M.L.; et al.; Synthetic studies leading to the identification of PNU-288034, a potent new oxazolidinone antibacterial agent. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1333. |
【2】 Zurenko, G.E.; Barbachyn, M.R. (Pharmacia Corp.); A thiazine oxazolidinone. EP 1294717; US 2002156072; US 6605609; WO 0198297 . |
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) | 62749 | 2,6-difluoro-4-nitrophenyl trifluoromethanesulfonate | C7H2F5NO5S | 详情 | 详情 | |
(II) | 36317 | thiomorpholine | 123-90-0 | C4H9NS | 详情 | 详情 |
(III) | 62750 | 4-(2,6-difluoro-4-nitrophenyl)thiomorpholine | C10H10F2N2O2S | 详情 | 详情 | |
(IV) | 62751 | 3,5-difluoro-4-(4-thiomorpholinyl)phenylamine; 3,5-difluoro-4-(4-thiomorpholinyl)aniline | C10H12F2N2S | 详情 | 详情 | |
(V) | 62752 | benzyl 3,5-difluoro-4-(4-thiomorpholinyl)phenylcarbamate | C18H18F2N2O2S | 详情 | 详情 | |
(VI) | 61915 | (1S)-2-(acetylamino)-1-(chloromethyl)ethyl acetate | C7H12ClNO3 | 详情 | 详情 | |
(VII) | 62753 | N-({(5S)-3-[3,5-difluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide | C16H19F2N3O3S | 详情 | 详情 |