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【结 构 式】

【分子编号】19752

【品名】(4S)-4-isopropyl-2-(2-quinolinyl)-1,3-oxazol-5(4H)-one

【CA登记号】

【 分 子 式 】C15H14N2O2

【 分 子 量 】254.28844

【元素组成】C 70.85% H 5.55% N 11.02% O 12.58%

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:(XX)

The condendsation of epoxide (V) with (2S,4R)(VI) by means of basic alumina in THF, followed by elimination of the protecting group with HCl and NaOH yields directly the condensation product (XVIII) as a pure diastereomer and with a free amino group. Finally, this compound is condensed with N-(2-quinolylcarbonyl)-L-valine (XIX) through its activation compound with isobutyl chloroformate (the 4(S)-isopropyl-2-(2-quinolyl)oxazol-5(4H)-one (XX)). The N-acyl-L-valine (XIX) has been obtained by acylation of L-valine (XXI) with quinoline-2-carboxylic acid (X) through its acyl chloride obtained with SOCl2.

1 Beaulieu, P.L.; et al.; Practical, stereoselective synthesis of palinavir, a potent HIV protease inhibitor. J Org Chem 1997, 62, 11, 3440.
2 Gillard, J.; et al.; Preparation of (2S,4R)-4-hydroxypipecolic acid and derivatives. J Org Chem 1996, 61, 6, 2226.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
14532 2-Quinolinecarboxylic acid; Quinaldic Acid 93-10-7 C10H7NO2 详情 详情
(V) 19730 tert-butyl (1S)-1-[(2S)oxiranyl]-2-phenylethylcarbamate 98737-29-2 C15H21NO3 详情 详情
(VI) 19731 (2S,4R)-N-(tert-butyl)-4-(4-pyridinylmethoxy)-2-piperidinecarboxamide C16H25N3O2 详情 详情
(XVIII) 19750 (2S,4R)-1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)-4-(4-pyridinylmethoxy)-2-piperidinecarboxamide C26H38N4O3 详情 详情
(XIX) 19751 (2S)-2-[(3-isoquinolinylcarbonyl)amino]-3-methylbutyric acid C15H16N2O3 详情 详情
(XX) 19752 (4S)-4-isopropyl-2-(2-quinolinyl)-1,3-oxazol-5(4H)-one C15H14N2O2 详情 详情
(XXI) 37828 L-2-Amino-3-methylbutyric acid; L-2-Aminoisovaleric acid; 2-Aminoisovaleric acid; L-2-Amino-3-methylbutyric acid; L-alpha-Aminoisovaleric acid; L-valine; (S)-(+)-Valine; (S)-alpha-Aminoisovaleric acid 72-18-4 C5H11NO2 详情 详情
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