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

【结 构 式】

【分子编号】62754

【品名】4-(2,6-difluorophenyl)-1lambda~6~,4-thiazinane-1,1-dione

【CA登记号】

【 分 子 式 】C10H11F2NO2S

【 分 子 量 】247.2656864

【元素组成】C 48.58% H 4.48% F 15.37% N 5.66% O 12.94% S 12.97%

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:(III)

In an improved procedure, conjugate addition of divinyl sulfone (II) to 2,6-difluoroaniline (I) in the presence of AlCl3 leads to the N-aryl thiomorpholine sulfone (III). Aromatic nitration of (III) with fuming HNO3 in AcOH affords (IV). The nitroaryl derivative (IV) is then reduced to aniline (V) by catalytic hydrogenation over Raney Ni. Condensation of aniline (V) with isobutyl chloroformate furnishes carbamate (VI). This is finally cyclized with (S)-N-(2-acetoxy-3-chloropropyl)acetamide (VII) to generate the target oxazolidinone 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) 17933 2,6-Difluorophenylamine; 2,6-Difluoroaniline 5509-65-9 C6H5F2N 详情 详情
(II) 35813 divinyl sulfone; dioxo(divinyl)-lambda(6)-sulfane 77-77-0 C4H6O2S 详情 详情
(III) 62754 4-(2,6-difluorophenyl)-1lambda~6~,4-thiazinane-1,1-dione C10H11F2NO2S 详情 详情
(IV) 62755 4-(2,6-difluoro-4-nitrophenyl)-1lambda~6~,4-thiazinane-1,1-dione C10H10F2N2O4S 详情 详情
(V) 62756 4-(4-amino-2,6-difluorophenyl)-1lambda~6~,4-thiazinane-1,1-dione C10H12F2N2O2S 详情 详情
(VI) 62757 isobutyl 4-(1,1-dioxo-1lambda~6~,4-thiazinan-4-yl)-3,5-difluorophenylcarbamate C15H20F2N2O4S 详情 详情
(VII) 61915 (1S)-2-(acetylamino)-1-(chloromethyl)ethyl acetate C7H12ClNO3 详情 详情
Extended Information