tert-butyl 7-({[bis(tert-butoxycarbonyl)amino]oxy}methyl)-2,2-dimethyl[1,3]dioxolo[4,5-g]quinoxaline-6-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】58724

【品名】tert-butyl 7-({[bis(tert-butoxycarbonyl)amino]oxy}methyl)-2,2-dimethyl[1,3]dioxolo[4,5-g]quinoxaline-6-carboxylate

【CA登记号】

【分子式】C₂₇H₃₇N₃O₉

【分子量】547.6056

【元素组成】C 59.22% H 6.81% N 7.67% O 26.3%

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：(VIII)

Quinoxaline (VI) was prepared by condensation of phenylenediamine (IV) with tert-butyl 2,3-dioxobutyrate (V). Radical bromination of (VI) using N-bromosuccinimide and AIBN furnished the bromomethyl quinoxaline (VII) as the major brominated compound. This was condensed with N,N-di-Boc-hydroxylamine (III) to afford the protected O-alkyl hydroxylamine (VIII). Then, treatment of (VIII) with hot concentrated HCl gave rise to the fully deprotected quinoxaline (IX).

参考文献中间体

合成目标

【1】 Koster, W.H.; Sundeen, J.E.; Straub, H.; Ermann, P.H.; Treuner, U. (Bristol-Myers Squibb Co.); Heteroaroyl derivs. of monocyclic beta-lactam antibiotics. EP 0484881; JP 1992283579 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(III)	58719	2-({[(tert-butoxycarbonyl)(hydroxy)amino]carbonyl}oxy)-2-methylpropane	C₁₀H₁₉NO₅	详情	详情
(IV)	58720	2,2-dimethyl-1,3-benzodioxole-5,6-diamine; 6-amino-2,2-dimethyl-1,3-benzodioxol-5-ylamine	C₉H₁₂N₂O₂	详情	详情
(V)	58721	tert-butyl 2,3-dioxobutanoate	C₈H₁₂O₄	详情	详情
(VI)	58722	tert-butyl 2,2,7-trimethyl[1,3]dioxolo[4,5-g]quinoxaline-6-carboxylate	C₁₇H₂₀N₂O₄	详情	详情
(VII)	58723	tert-butyl 7-(bromomethyl)-2,2-dimethyl[1,3]dioxolo[4,5-g]quinoxaline-6-carboxylate	C₁₇H₁₉BrN₂O₄	详情	详情
(VIII)	58724	tert-butyl 7-({[bis(tert-butoxycarbonyl)amino]oxy}methyl)-2,2-dimethyl[1,3]dioxolo[4,5-g]quinoxaline-6-carboxylate	C₂₇H₃₇N₃O₉	详情	详情
(IX)	58725	3-[(aminooxy)methyl]-6,7-dihydroxy-2-quinoxalinecarboxylic acid	C₁₀H₉N₃O₅	详情	详情

Extended Information