【结 构 式】 |
【分子编号】64122 【品名】[1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]methylhydrosulfide; [1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]methanethiol 【CA登记号】 |
【 分 子 式 】C11H13FN2O2S 【 分 子 量 】256.3009032 【元素组成】C 51.55% H 5.11% F 7.41% N 10.93% O 12.48% S 12.51% |
合成路线1
该中间体在本合成路线中的序号:(VI)Condensation between 1,2-difluoro-4-nitrobenzene (I) and L-prolinol (II) affords the N-aryl prolinol (III). Subsequent conversion of alcohol (III) into bromide (IV) is achieved by treatment with CBr4 and PPh3. Displacement of bromide (IV) with sodium thioacetate, followed by basic hydrolysis of the resultant thioacetate ester (V) leads to thiol (VI). Intramolecular cyclization of (VI) in the presence of NaH generates the pyrrolobenzothiazine system (VII). Catalytic hydrogenation of the nitro group of (VII) gives amine (VIII), which is acylated by benzyl chloroformate to provide carbamate (IX). The lithium anion of carbamate (IX) is condensed with (R)-glycidyl butyrate (X) to furnish oxazolidinone (XI). Then, treatment of alcohol (XI) with methanesulfonyl chloride produces mesylate (XII).
【1】 Selvakumar, N.; Reddy, B.Y.; Kumar, G.S.; Khera, M.K.; Srinivas, D.; Kumar, M.S.; Das, J.; Iqbal, J.; Trehan, S.; SAR studies on certain conformationally constrained oxazolidinones. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1324. |
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) | 17013 | 1,2-difluoro-4-nitrobenzene; 3,4-Difluoronitrobenzene | 369-34-6 | C6H3F2NO2 | 详情 | 详情 |
(II) | 64118 | (2S)pyrrolidinylmethanol | C5H11NO | 详情 | 详情 | |
(III) | 64119 | [1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]methanol | C11H13FN2O3 | 详情 | 详情 | |
(IV) | 64120 | 2-(bromomethyl)-1-(2-fluoro-4-nitrophenyl)pyrrolidine | C11H12BrFN2O2 | 详情 | 详情 | |
(V) | 64121 | S-{[1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]methyl} ethanethioate | C13H15FN2O3S | 详情 | 详情 | |
(VI) | 64122 | [1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]methylhydrosulfide; [1-(2-fluoro-4-nitrophenyl)-2-pyrrolidinyl]methanethiol | C11H13FN2O2S | 详情 | 详情 | |
(VII) | 64123 | 7-nitro-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazine | C11H12N2O2S | 详情 | 详情 | |
(VIII) | 64124 | 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazin-7-ylamine; 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazin-7-amine | C11H14N2S | 详情 | 详情 | |
(IX) | 64125 | phenylmethyl 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazin-7-ylcarbamate | C19H20N2O2S | 详情 | 详情 | |
(X) | 18385 | (2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate | 60456-26-0 | C7H12O3 | 详情 | 详情 |
(XI) | 64126 | 3-(2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazin-7-yl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one | C15H18N2O3S | 详情 | 详情 | |
(XII) | 64127 | [3-(2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzothiazin-7-yl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate | C16H20N2O5S2 | 详情 | 详情 |