6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid -Drug Synthesis Database

【结构式】

【分子编号】63203

【品名】6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid

【CA登记号】

【分子式】C₁₀H₁₃NO₄

【分子量】211.21756

【元素组成】C 56.87% H 6.2% N 6.63% O 30.3%

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：(III)

6-Aminocaproic acid (I) is condensed with maleic anhydride (II) in refluxing AcOH to provide maleimidocaproic acid (III). After activation of acid (III) as the corresponding mixed anhydride with isobutyl chloroformate, coupling with tert-butyl carbazate (IV) affords the N-Boc hydrazide (V). Subsequent acidic cleavage of the Boc group of (V) furnishes hydrazide (VI). Finally, hydrazide (VI) is condensed with doxorubicin (VII) to produce the title hydrazone conjugate.

参考文献中间体

合成目标

【1】 Willner, D.; Trail, P.A.; Hofstead, S.J.; King, H.D.; Lasch, S.J.; Braslawsky, G.R.; Greenfield, R.S.; Kaneko, T.; Firestone, R.A.; (6-Maleimidocaproyl)hydrazone of doxorubicin - A new derivative for the preparation of immunoconjugates of doxorubicin. Bioconjugate Chem 1993, 4, 6, 521.
【2】 Willner, D.; Trail, P.A.; King, D.H.; Hofstead, S.J.; Greenfield, R.S.; Braslawsky, G.R. (Bristol-Myers Squibb Co.); Thioether conjugates. EP 0554708; JP 1994025012; US 5622929 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	41170	6-aminohexanoic acid	60-32-2	C₆H₁₃NO₂	详情	详情
(II)	11182	2,5-Furandione; Maleic anhydride	108-31-6	C₄H₂O₃	详情	详情
(III)	63203	6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid		C₁₀H₁₃NO₄	详情	详情
(IV)	10893	tert-butyl 1-hydrazinecarboxylate; tert-butyl carbazate	870-46-2	C₅H₁₂N₂O₂	详情	详情
(V)	63204	tert-butyl 2-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-1-hydrazinecarboxylate		C₁₅H₂₃N₃O₅	详情	详情
(VI)	63205	6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanohydrazide		C₁₀H₁₅N₃O₃	详情	详情
(VII)	11675	(8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione		C₂₇H₂₉NO₁₁	详情	详情

Extended Information