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【结 构 式】

【分子编号】44401

【品名】tert-butyl (2S)-1-[[(2S)-2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-yl]carbonyl]-2-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C20H28N2O3S

【 分 子 量 】376.52

【元素组成】C 63.8% H 7.5% N 7.44% O 12.75% S 8.52%

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:(S,S)-(III)

The condensation of 2-(3-pyridinyl)tetrahydrothiopyran-2-carboxylic acid (I) with L-proline tert-butyl ester (II) by means of SOCl2 gives the corresponding amide as a diastereomeric mixture (S,S)-(III) + (R,S)-(III) that is separated by chromatography. The desired isomer (R,S)-(III) is hydrolyzed with conc. HCl to yield 2-(3-pyridinyl)tetrahydrothiopyran-2-carboxylic acid (R)-(IV), which is treated first with SOCl2 and methylamine, and then with Lawesson reagent or P2S5 to afford the thioamide (R)-(V). The reaction of (R)-(V) with methyl iodide, n-BuLi and H2S in pyridine provides the dithioester (R)-(VI), which is carefully oxidized with MCPBA in dichloromethane to provide the corresponding sulfoxide as a diastereomeric mixture (1R,2R)-(VII) + (1S,2R)-(VII) that is separated by chromatography. Finally, the desired isomer (1R,2R)-(VII) is treated with methylamine in ethanol to furnish the target thioamide.

1 Aloup, J.C.; Farge, D.; James, C.; Mondot, S.; Cavero, I.; 2-(3-PYRIDYL)-TETRAHYDROTHIOPYRAN-2-CARBOTHIOAMIDE DERIVATIVES AND ANALOGUES: A NOVEL FAMILY OF POTENT POTASSIUM CHANNEL OPENERS. Drugs Fut 1990, 15, 11, 1097.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(S,S)-(III) 44401 tert-butyl (2S)-1-[[(2S)-2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-yl]carbonyl]-2-pyrrolidinecarboxylate C20H28N2O3S 详情 详情
(R,S)-(III) 44402 tert-butyl (2S)-1-[[(2R)-2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-yl]carbonyl]-2-pyrrolidinecarboxylate C20H28N2O3S 详情 详情
(1R,2S)-(VII) 44406 methyl (2R)-1-oxo-2-(3-pyridinyl)hexahydro-1lambda(4)-thiopyran-2-carbodithioate C12H15NOS3 详情 详情
(1S,2R)-(VII) 44407 methyl (2R)-1-oxo-2-(3-pyridinyl)hexahydro-1lambda(4)-thiopyran-2-carbodithioate C12H15NOS3 详情 详情
(I) 44400 2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-carboxylic acid C11H13NO2S 详情 详情
(II) 19832 tert-butyl (2S)-2-pyrrolidinecarboxylate C9H17NO2 详情 详情
(IV) 44403 (2R)-2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-carboxylic acid C11H13NO2S 详情 详情
(V) 44404 (2R)-N-methyl-2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-carbothioamide C12H16N2S2 详情 详情
(VI) 44405 methyl (2R)-2-(3-pyridinyl)tetrahydro-2H-thiopyran-2-carbodithioate C12H15NS3 详情 详情
Extended Information