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【结 构 式】

【分子编号】38550

【品名】methyl (2S)-3-methyl-2-[2-oxotetrahydro-1(2H)-pyrimidinyl]butanoate

【CA登记号】

【 分 子 式 】C10H18N2O3

【 分 子 量 】214.2646

【元素组成】C 56.06% H 8.47% N 13.07% O 22.4%

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:(XXI)

The intermediate 3-methyl 2(S)-(2-oxoperhydropyrimidin1-yl)butyric acid (XIII) has been obtained as follows: The oxidation of 3-(benzyloxycarbonylamino)-1-propanol (XVII) with oxalyl chloride in dichloromethane gives the corresponding aldehyde (XVIII), which is reductocondensed with L-valine methyl ester (XIX) by means NaBH3CN in methanol yielding the N-substituted valine (XX). The cyclization of (XX) by elimination of the benzyloxycarbonyl group by hydrogenation with H2 over Pd/C in dichloromethane, followed by reaction with carbonyldiimidazole (CDI) affords the 3-methyl 2(S)-(2-oxoperhydropyrimidin-1-yl)butyric acid methyl ester (XXI). Finally, this compound is hydrolyzed with LiOH in dioxane/water to afford the target intermediate (XIII).

1 Retroviral protease inhibiting cpds.. EP 0882024; JP 2000502085; US 5914332; WO 9721685 .
2 Sham, H.L.; Stewart, K.D.; Kempf, D.J. (Abbott Laboratories Inc.); Retroviral protease inhibiting cpds.. EP 0876353; JP 2000502997; WO 9721683 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 38264 (2S)-3-methyl-2-[2-oxotetrahydro-1(2H)-pyrimidinyl]butyric acid C9H16N2O3 详情 详情
(XVII) 38547 benzyl 3-hydroxypropylcarbamate C11H15NO3 详情 详情
(XVIII) 38548 benzyl 3-oxopropylcarbamate C11H13NO3 详情 详情
(XIX) 16613 methyl (2S)-2-amino-3-methylbutanoate C6H13NO2 详情 详情
(XX) 38549 methyl (2S)-2-[(3-[[(benzyloxy)carbonyl]amino]propyl)amino]-3-methylbutanoate C17H26N2O4 详情 详情
(XXI) 38550 methyl (2S)-3-methyl-2-[2-oxotetrahydro-1(2H)-pyrimidinyl]butanoate C10H18N2O3 详情 详情
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