10-[[2-(acetoxy)benzoyl]amino]decanoic acid -Drug Synthesis Database

【结构式】

【分子编号】43264

【品名】10-[[2-(acetoxy)benzoyl]amino]decanoic acid

【CA登记号】

【分子式】C₁₉H₂₇NO₅

【分子量】349.42712

【元素组成】C 65.31% H 7.79% N 4.01% O 22.89%

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：(VII)

Conversion of 10-undecen-1-ol (I) into the primary amine (IV) was effected by Mitsunobu coupling of (I) with phthalimide (II), followed by hydrazinolysis of the resulting N-(10-undecenyl)phthalimide (III). Amine (IV) was then acylated with O-acetylsalicyloyl chloride (V) to give salicylamide (VI). Oxidative cleavage of the terminal olefin to the carboxylic acid (VII) was achieved using potassium permanganate under phase-transfer conditions. The O-acetyl group was finally removed by treatment with NaOH.

参考文献中间体

合成目标

【1】 Leone-Bay, A.; Paton, D.R.; Freeman, J.; et al.; Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J Med Chem 1998, 41, 7, 1163.
【2】 Leone-Bay, A.; Ho, K.-K.; Sarubbi, D.J.; Milstein, S.J.; Press, J.B. (Emisphere Technologies, Inc.); Cpds. and compsns. for delivering active agents. US 5650386; WO 9630036 .
【3】 Leone-Bay, A. (Emisphere Technologies, Inc.); Cpds. and compsns. for delivering active agents. WO 9736480 .

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)	43260	10-undecen-1-ol	112-43-6	C₁₁H₂₂O	详情	详情
(II)	12376	Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione	85-41-6	C₈H₅NO₂	详情	详情
(III)	43261	2-(10-undecenyl)-1H-isoindole-1,3(2H)-dione		C₁₉H₂₅NO₂	详情	详情
(IV)	43262	10-undecenylamine; 10-undecen-1-amine		C₁₁H₂₃N	详情	详情
(V)	16900	2-(chlorocarbonyl)phenyl acetate; Acetylsalicyloyl chloride	5538-51-2	C₉H₇ClO₃	详情	详情
(VI)	43263	2-[(10-undecenylamino)carbonyl]phenyl acetate		C₂₀H₂₉NO₃	详情	详情
(VII)	43264	10-[[2-(acetoxy)benzoyl]amino]decanoic acid		C₁₉H₂₇NO₅	详情	详情

Extended Information