2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)dodecanoic acid -Drug Synthesis Database

【结构式】

【分子编号】63518

【品名】2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)dodecanoic acid

【CA登记号】

【分子式】C₁₇H₃₃NO₄

【分子量】315.45336

【元素组成】C 64.73% H 10.54% N 4.44% O 20.29%

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：(V)

Alkylation of diethyl acetamidomalonate (I) with 1-bromodecane (II) affords malonate (III). Subsequent hydrolysis and decarboxylation of (III) under acidic conditions leads to 2-aminododecanoic acid (IV). This is then protected as the N-Boc derivative (V) upon treatment with Boc2O and NaOH

参考文献中间体

合成目标

【1】 Blanchfield, J.T.; Dutton, J.L.; Hogg, R.C.; Gallagher, O.P.; Craik, D.J.; Jones, A.; Adams, D.J.; Lewis, R.J..; Alewood, P.F.; Toth, I.; Synthesis, structure elucidation, in vitro biological activity, toxicity, and caco-2 cell permeability of lipophilic analogues of alpha-conotoxin MII. J Med Chem 2003, 46, 7, 1266.

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)	16710	Diethyl 2-(acetamido)malonate; Diethyl acetamidomalonate	1068-90-2	C₉H₁₅NO₅	详情	详情
(II)	58570	1-Bromodecane; 1-Decyl bromide; Decyl bromide; n-decyl bromide	112-29-8	C₁₀H₂₁Br	详情	详情
(III)	63516	diethyl 2-(acetylamino)-2-decylpropanedioate		C₁₉H₃₅NO₅	详情	详情
(IV)	63517	2-aminododecanoic acid		C₁₂H₂₅NO₂	详情	详情
(V)	63518	2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)dodecanoic acid		C₁₇H₃₃NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The protected peptide-bound resin (VI) is prepared by solid-phase synthesis on a p-methylbenzhydrylamine resin, using HBTU/DIEA activation. Coupling of 2-(Boc-amino)dodecanoic acid (V) to the peptide resin (VI) by means of HBTU affords amide (VII). The DNP protecting groups of the histidine residues of (VII) are subsequently removed by treatment with 2-mercaptoethanol to provide (VIII). Further acidic cleavage of the N-terminal Boc group of (VIII) with trifluoroacetic acid leads to resin (IX). The linear peptide (X) is then cleaved from the resin by treatment with liquid (HF) in the presence of p-thiocresol

参考文献中间体

合成目标

【1】 Blanchfield, J.T.; Dutton, J.L.; Hogg, R.C.; Gallagher, O.P.; Craik, D.J.; Jones, A.; Adams, D.J.; Lewis, R.J..; Alewood, P.F.; Toth, I.; Synthesis, structure elucidation, in vitro biological activity, toxicity, and caco-2 cell permeability of lipophilic analogues of alpha-conotoxin MII. J Med Chem 2003, 46, 7, 1266.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	63518	2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)dodecanoic acid		C₁₇H₃₃NO₄	详情	详情

Extended Information