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【结 构 式】

【药物名称】PNU-173995

【化学名称】N-[3-[3-Fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxooxazolidin-5(S)-ylmethyl]thioacetamide

【CA登记号】216868-84-7

【 分 子 式 】C18H23FN4O4S

【 分 子 量 】410.47081

【开发单位】Pfizer (Originator)

【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Oxazolidinones

合成路线1

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
Extended Information