benzyl 2-cyclopentyl-10-iododecanoate -Drug Synthesis Database

【结构式】

【分子编号】49103

【品名】benzyl 2-cyclopentyl-10-iododecanoate

【CA登记号】

【分子式】C₂₂H₃₃IO₂

【分子量】456.40729

【元素组成】C 57.9% H 7.29% I 27.81% O 7.01%

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：(XI)

After conversion of cyclopentylacetic acid (IX) to the corresponding benzyl ester (X), alkylation with 1,8-diiodooctane in the presence of LDA generated the iodo ester (XI). Iodide displacement in (XI) with potassium phthalimide (XII) in hot DMF produced the substituted phthalimide (XIII). Then, hydrogenolysis of the benzyl ester group of (XIII) furnished carboxylic acid (XIV). Acylation of the intermediate dipeptide (VIII) with acid (XIV) by using BOP and HOBt yielded amide (XV). Finally, acid hydrolysis of the diethyl acetal function of (XV) gave rise to the title aldehyde.

参考文献中间体

合成目标

【1】 Iqbal, M.; et al.; Potent inhibitors of proteasome. J Med Chem 1995, 38, 13, 2276.
【2】 Iqbal, M.; Diebold, J.; Siman, R.; Chatterjee, S.; Kauer, J.C. (Cephalon, Inc.); Multicatalytic protease inhibitors. JP 1998507465; JP 2000290197; WO 9614857 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	49100			C₁₆H₃₄N₆O₅	详情	详情
(IX)	49101	Cyclopentylacetic acid	1123-00-8	C₇H₁₂O₂	详情	详情
(X)	49102	benzyl 2-cyclopentylacetate		C₁₄H₁₈O₂	详情	详情
(XI)	49103	benzyl 2-cyclopentyl-10-iododecanoate		C₂₂H₃₃IO₂	详情	详情
(XII)	27890	Potassium phthalimide	1074-82-4	C₈H₄KNO₂	详情	详情
(XIII)	49104	benzyl 2-cyclopentyl-10-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)decanoate		C₃₀H₃₇NO₄	详情	详情
(XIV)	49105	2-cyclopentyl-10-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)decanoic acid		C₂₃H₃₁NO₄	详情	详情
(XV)	49106			C₃₉H₆₃N₇O₈	详情	详情

Extended Information