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【结 构 式】

【分子编号】55851

【品名】Ethyl dithioacetate

【CA登记号】

【 分 子 式 】C4H8S2

【 分 子 量 】120.23952

【元素组成】C 39.96% H 6.71% S 53.34%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IX)

Deprotection of the benzyloxycarbonyl piperazine (I) by catalytic hydrogenolysis provided the secondary amine (II), which was then acylated by benzyloxyacetyl chloride (III) to afford amide (IV). After activation of the hydroxyl group of (IV) as the sulfonate (VI) by treatment with 3-nitrobenzenesulfonyl chloride (V), its displacement with ammonium hydroxide provided the amine (VII). The O-benzyl group of (VII) was then removed by hydrogenolysis, yielding alcohol (VIII). Finally, acylation of the primary amino group of (VIII) with ethyl dithioacetate (IX) in the presence of KOH and NaF gave rise to the title thioacetamide.

1 Hester, J.B. Jr.; Perricone, S.C.; Nidy, E.G.; Poel, T.-J. (Pharmacia Corp.); Oxazolidinone antibacterial agents having a thiocarbonyl functionality. EP 0984947; JP 2002501530; US 6218413; WO 9854161 .
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) 18386 benzyl 4-[2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]-1-piperazinecarboxylate C22H24FN3O5 详情 详情
(II) 55847 (5R)-3-[3-fluoro-4-(1-piperazinyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one C14H18FN3O3 详情 详情
(III) 10493 2-(Benzyloxy)acetyl chloride; Benzyloxyacetyl chloride 19810-31-2 C9H9ClO2 详情 详情
(IV) 55848 (5R)-3-(4-{4-[2-(benzyloxy)acetyl]-1-piperazinyl}-3-fluorophenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one C23H26FN3O5 详情 详情
(V) 41948 3-nitrobenzenesulfonyl chloride 121-51-7 C6H4ClNO4S 详情 详情
(VI) 55849 [(5R)-3-(4-{4-[2-(benzyloxy)acetyl]-1-piperazinyl}-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl 3-nitrobenzenesulfonate C29H29FN4O9S 详情 详情
(VII) 55850 (5S)-5-(aminomethyl)-3-(4-{4-[2-(benzyloxy)acetyl]-1-piperazinyl}-3-fluorophenyl)-1,3-oxazolidin-2-one C23H27FN4O4 详情 详情
(VIII) 17828 (5S)-5-(aminomethyl)-3-[3-fluoro-4-(4-glycoloyl-1-piperazinyl)phenyl]-1,3-oxazolidin-2-one C16H21FN4O4 详情 详情
(IX) 55851 Ethyl dithioacetate C4H8S2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(III)

The azidomethyl oxazolidinone (I) was reduced to the corresponding amine (II) by treatment with triphenylphosphine, followed by aqueous hydrolysis of the intermediate iminophosphorane. Condensation of amine (II) with ethyl dithioacetate (III) produced thioacetamide (IV). After acidic cleavage of the tert-butyl ester, the resultant carboxylic acid (V) was converted to the active ester (VI) upon treatment with pentafluorophenyl trifluoroacetate. Finally, displacement of the pentafluorophenyl ester (VI) with methylamine gave rise to the target N-methyl amide.

1 Luehr, G.W.; Gordeev, M.F.; Gadwood, R.C.; et al.; 4'-Amido phenyloxazolidinone thioamides: Antimicrobial activity and pharmacokinetics in rat. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-1047.
2 Patel, D.V.; Gadwood, R.C.; Gordeev, M.F.; Luehr, G.W. (Pharmacia Corp.); Oxazolidinones and their use as antiinfectives. EP 1200416; US 6441005; WO 0109107 .
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) 55908 tert-butyl 4-[(5R)-5-(azidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorobenzoate C15H17FN4O4 详情 详情
(II) 58767 tert-butyl 4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorobenzoate C15H19FN2O4 详情 详情
(III) 55851 Ethyl dithioacetate C4H8S2 详情 详情
(IV) 58768 tert-butyl 4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorobenzoate C17H21FN2O4S 详情 详情
(V) 58769 4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorobenzoic acid C13H13FN2O4S 详情 详情
(VI) 58770 2,3,4,5,6-pentafluorophenyl 4-{(5S)-5-[(ethanethioylamino)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorobenzoate C19H12F6N2O4S 详情 详情
Extended Information