2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】48363

【品名】2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylic acid

【CA登记号】

【分子式】C₁₂H₁₈N₂O₅

【分子量】270.2854

【元素组成】C 53.33% H 6.71% N 10.36% O 29.6%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

The heterocyclic amino acid precursor (VI) was synthesized as follows. Coupling between N-Boc-D-alanine (I) and L-threonine methyl ester (II) in the presence of DCC and HOBt gave dipeptide (III). Cyclization of (III) using Burgess reagent provided the oxazoline (IV) as a mixture of diastereoisomers. Subsequent dehydrogenation of (IV) by means of bromotrichloromethane and DBU afforded the protected oxazole amino acid (V). Basic hydrolysis of the ethyl ester group then yielded the intermediate acid (VI).

参考文献中间体

合成目标

【1】 Xia, Z.; Smith, C.D.; Total synthesis of dendroamide A, a novel cyclic peptide that reverses multiple drug resistance. J Org Chem 2001, 66, 10, 3459.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IVa)	48360	methyl (4S,5R)-2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate		C₁₃H₂₂N₂O₅	详情	详情
(IVb)	48361	methyl (4S,5S)-2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate		C₁₃H₂₂N₂O₅	详情	详情
(I)	15859	Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid	7764-95-6	C₈H₁₅NO₄	详情	详情
(II)	42026	methyl (2S,3R)-2-amino-3-hydroxybutanoate		C₅H₁₁NO₃	详情	详情
(III)	48359	methyl (2S,3R)-2-([(2R)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)-3-hydroxybutanoate		C₁₃H₂₄N₂O₆	详情	详情
(V)	48362	methyl 2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylate		C₁₃H₂₀N₂O₅	详情	详情
(VI)	48363	2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylic acid		C₁₂H₁₈N₂O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The intermediate acid (VI) was then coupled to amine (XXI) to furnish (XXII). Sequential deprotection of the ethyl ester and the N-Boc protecting groups of (XXII) produced the linear precursor (XXIV). This was finally cyclized to the title compound using DPPA.

参考文献中间体

合成目标

【1】 Xia, Z.; Smith, C.D.; Total synthesis of dendroamide A, a novel cyclic peptide that reverses multiple drug resistance. J Org Chem 2001, 66, 10, 3459.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	48363	2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazole-4-carboxylic acid	C₁₂H₁₈N₂O₅	详情	详情
(XXI)	48374	ethyl 2-[(1R)-1-[([2-[(1R)-1-amino-2-methylpropyl]-1,3-thiazol-4-yl]carbonyl)amino]ethyl]-1,3-thiazole-4-carboxylate	C₁₆H₂₂N₄O₃S₂	详情	详情
(XXII)	48376	ethyl 2-[(1R)-1-([[2-((1R)-1-[[(2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazol-4-yl)carbonyl]amino]-2-methylpropyl)-1,3-thiazol-4-yl]carbonyl]amino)ethyl]-1,3-thiazole-4-carboxylate	C₂₈H₃₈N₆O₇S₂	详情	详情
(XXIII)	48377	2-[(1R)-1-([[2-((1R)-1-[[(2-[(1R)-1-[(tert-butoxycarbonyl)amino]ethyl]-5-methyl-1,3-oxazol-4-yl)carbonyl]amino]-2-methylpropyl)-1,3-thiazol-4-yl]carbonyl]amino)ethyl]-1,3-thiazole-4-carboxylic acid	C₂₆H₃₄N₆O₇S₂	详情	详情
(XXIV)	48378	2-((1R)-1-[[(2-[(1R)-1-[([2-[(1R)-1-aminoethyl]-5-methyl-1,3-oxazol-4-yl]carbonyl)amino]-2-methylpropyl]-1,3-thiazol-4-yl)carbonyl]amino]ethyl)-1,3-thiazole-4-carboxylic acid	C₂₁H₂₆N₆O₅S₂	详情	详情

Extended Information