tert-butyl 3-oxo-1-piperazinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】44877

【品名】tert-butyl 3-oxo-1-piperazinecarboxylate

【CA登记号】

【分子式】C₉H₁₆N₂O₃

【分子量】200.23772

【元素组成】C 53.99% H 8.05% N 13.99% O 23.97%

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)

Synthesis of intermediate (VI): Treatment of 2-oxopiperazine (I) with di-t-butyl dicarbonate (II) and Et3N in DMF affords 1-t-butoxycarbonyl-3-oxopiperazine (III), which is then condensed with bromo derivative (IV) by means of NaH in THF, providing ethyl phenoxyacetate derivative (V). Treatment of (V) with HCl/EtOAc allows removal of the t-butyloxycarbonyl group, yielding intermediate (VI). Alternatively, intermediate (VI) can be obtained by first formylation of (I) with formic acid and acetic anhydride (Ac2O) in CH2Cl2 to afford derivative (VII), followed by condensation of (VII) with (IV) to give (VIII) by means of NaH in DMF/THF and deformylation by treatment with HCl/EtOAc to afford (VI).

参考文献中间体

合成目标

【1】 Ohuchi, S.; Suzuki, H.; Ando, T.; Katano, K.; Imai, T.; Kobayashi, K.; Ota, K.; Aizawa, K.; Miura, T. (Meiji Seika Kaisha, Ltd.); Nitrogen-containing heterocyclic cpds. having antiplatelet aggregation effect and medicinal use thereof. EP 1070712; WO 9952894 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	44876	2-piperazinone	C₄H₈N₂O	详情	详情
(II)	11147	di(tert-butyl) carbonate	C₉H₁₈O₃	详情	详情
(III)	44877	tert-butyl 3-oxo-1-piperazinecarboxylate	C₉H₁₆N₂O₃	详情	详情
(IV)	44878	ethyl 2-[4-(1lambda(3)-dibromanylcarbonyl)phenoxy]acetate	C₁₁H₁₂Br₂O₄	详情	详情
(V)	44879	tert-butyl 4-[2-[4-(2-ethoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-3-oxo-1-piperazinecarboxylate	C₂₁H₂₈N₂O₇	详情	详情
(VI)	44880	ethyl 2-[4-[2-(2-oxo-1-piperazinyl)acetyl]phenoxy]acetate	C₁₆H₂₀N₂O₅	详情	详情
(VII)	44881	3-oxo-1-piperazinecarbaldehyde	C₅H₈N₂O₂	详情	详情
(VIII)	44882	ethyl 2-[4-[2-(4-formyl-2-oxo-1-piperazinyl)acetyl]phenoxy]acetate	C₁₇H₂₀N₂O₆	详情	详情

Extended Information