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【结 构 式】 
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【分子编号】37579 【品名】methyl 5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoate 【CA登记号】 |
【 分 子 式 】C14H18N2O5 【 分 子 量 】294.3074 【元素组成】C 57.14% H 6.16% N 9.52% O 27.18% |
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：(II)The esterification of N2-(benzyloxycarbonyl)-D,L-glutamine (I) with methyl iodide and KHCO3 in DMF gives the corresponding methyl ester (II), which is cyclized to benzyl D,L-2,6-dioxo-3-piperidinecarbamate (III) by heating. The hydrogenolysis of (III) with H2 over Pd/C in methanol yields D,L-2-aminoglutarimide (IV), which is condensed with 2-chloroethyl isocyanate (V) in DMF affording 1-(2-chloroethyl)-3-(2,6-dioxo-3-piperidyl)urea (VI). Finally, this compound is nitrosated in the usual way with NaNO2 in formic acid.
| 【1】 Johnston, T.P.; et al.; The synthesis of potential anticancer agents. XXXVI. N-Nitrosoureas. II. Haloalkyl derivatives. J Med Chem 1966, 9, 6, 892-911. |
| 【2】 Woodman, R.J.; Castaner, J.; PCNU. Drugs Fut 1981, 6, 8, 481. |
| 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) | 37578 | N(2)-[(benzyloxy)carbonyl]glutamine | C13H16N2O5 | 详情 | 详情 | |
| (II) | 37579 | methyl 5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoate | C14H18N2O5 | 详情 | 详情 | |
| (III) | 37575 | benzyl 2,6-dioxo-3-piperidinylcarbamate | C13H14N2O4 | 详情 | 详情 | |
| (IV) | 37576 | 3-amino-2,6-piperidinedione；3-aminopiperidine-2,6-dione；2-amino-Glutarimide；Glutamimide;a-Aminoglutarimide | 2353-44-8 | C5H8N2O2 | 详情 | 详情 |
| (V) | 11237 | 1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate | 1943-83-5 | C3H4ClNO | 详情 | 详情 |
| (VI) | 37577 | N-(2-chloroethyl)-N'-(2,6-dioxo-3-piperidinyl)urea | C8H12ClN3O3 | 详情 | 详情 |
Extended Information