(2S,4R)-1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)-4-(4-pyridinylmethoxy)-2-piperidinecarboxamide -Drug Synthesis Database

【结构式】

【分子编号】19750

【品名】(2S,4R)-1-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)-4-(4-pyridinylmethoxy)-2-piperidinecarboxamide

【CA登记号】

【分子式】C₂₆H₃₈N₄O₃

【分子量】454.61288

【元素组成】C 68.69% H 8.43% N 12.32% O 10.56%

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：(XVIII)

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.

参考文献中间体

合成目标

【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

Extended Information