• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【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%

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)

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
Extended Information