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【结 构 式】

【分子编号】39049

【品名】methyl 2-(4-methyl-3,6-dioxo-2-piperazinyl)acetate

【CA登记号】

【 分 子 式 】C8H12N2O4

【 分 子 量 】200.19436

【元素组成】C 48% H 6.04% N 13.99% O 31.97%

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:(IV)

Condensation of dimethyl aspartate (II) with benzyloxy carbonyl sarcosine (I) using DCI gave dimethyl benzyloxycarbonyl sarcosylaspartate (III). Removal of benzyloxycarbonyl function from (III) by catalytic hydrogenation or HBr-AcOH followed by cyclization, effected by storage over P2O5 in vacuo for 48 h, gave methyl (1-methyl-2,5-dioxopiperazin-3-yl)acetate (IV). When (IV) was reacted with ethylamine in a sealed tube for 36 h, it yielded N-ethyl-2-(1-methyl-2,5,dioxopiperazin-3-yl)acetamide (V). The compound (V) was reduced with LiAlH4 to give 1-methyl-3-(2-ethylamino)ethylpiperazine (VI). When (VI) was condensed with ethyl chloroformate (A) at pH 3-3.5, a mixture of monocarbamates (VIIa, VIIb) were obtained. Cyclization of the monocarbamates (VIIa, VIIb) were effected by treatment with sodium ethoxide to afford 3-ethyl-8-methyl-1,3,8-triazabicyclo[4.4.0]decan-2-one (centperazine). When (VI) was reacted with ethyl chloroformate (A) in the presence of NaOC2H5 or Et3N, the dicarbamate (VIII) was formed.

1 Saxena, R.; et al.; Studies in potential filaricides. 5. 3-Ethyl-8-methyl-1,3,8-triazabicyclo[4.4.0]decan-2-one, a new antifilarial agent. J Med Chem 1971, 14, 10, 929.
2 Arya, V.P.; Centperazine. Drugs Fut 1980, 5, 5, 229.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 12229 (2R,3S)-5,5-Dimethoxy-3-(phenylselanyl)-1,2-pentanediol C13H20O4Se 详情 详情
(VIIa) 39052 ethyl ethyl[2-(4-methyl-2-piperazinyl)ethyl]carbamate C12H25N3O2 详情 详情
(VIIb) 39053 ethyl 2-[2-(ethylamino)ethyl]-4-methyl-1-piperazinecarboxylate C12H25N3O2 详情 详情
(I) 39046 (benzyloxy)carbonyl(methyl)carbamic acid C10H11NO4 详情 详情
(II) 39047 dimethyl 2-aminosuccinate C6H11NO4 详情 详情
(III) 39048 dimethyl 2-([2-[[(benzyloxy)carbonyl](methyl)amino]acetyl]amino)succinate C17H22N2O7 详情 详情
(IV) 39049 methyl 2-(4-methyl-3,6-dioxo-2-piperazinyl)acetate C8H12N2O4 详情 详情
(V) 39050 N-ethyl-2-(4-methyl-3,6-dioxo-2-piperazinyl)acetamide C9H15N3O3 详情 详情
(VI) 39051 N-ethyl-2-(4-methyl-2-piperazinyl)-1-ethanamine; N-ethyl-N-[2-(4-methyl-2-piperazinyl)ethyl]amine C9H21N3 详情 详情
(VIII) 39054 ethyl 2-[2-[(ethoxycarbonyl)(ethyl)amino]ethyl]-4-methyl-1-piperazinecarboxylate C15H29N3O4 详情 详情
Extended Information