(2S)-2-([(2R)-2-[allyl(tert-butoxycarbonyl)amino]propanoyl]amino)propionic acid -Drug Synthesis Database

【结构式】

【分子编号】20695

【品名】(2S)-2-([(2R)-2-[allyl(tert-butoxycarbonyl)amino]propanoyl]amino)propionic acid

【CA登记号】

【分子式】C₁₄H₂₄N₂O₅

【分子量】300.35504

【元素组成】C 55.99% H 8.05% N 9.33% O 26.63%

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：(IX)

Alternatively, a chiral synthesis of intermediate (V) was developed from enantiopure amino acids. N-Boc-D-alanine (VI) was N-alkylated with allyl bromide in the presence of two equivalents of NaH, and the resulting N-allyl amino acid (VII) was coupled with L-alanine methyl ester (VIII) using 1-dimethylaminopropyl-3-ethylcarbodiimide (DEC) to provide dipeptide (IX). Subsequent acid treatment of (IX) produced both Boc deprotection and cyclization to the diketopiperazine (X), which was finally reduced to piperazine (V) with LiAlH4.

参考文献中间体

合成目标

【1】 Chang, K.-J.; Bishop, M.J.; Bubacz, D.G.; McNutt, R.W. Jr. (Glaxo Wellcome plc); Piperazine cpds. used in therapy. EP 0711289; JP 1997501156; WO 9504051 .
【2】 Chang, K.; Boswell, G.E.; Bubacz, D.G.; Collins, M.A.; Davis, A.O.; McNutt, R.W. (Delta Pharmaceuticals, Inc.); Opioid diarylmethylpiperazines and piperidines. JP 1995503247; US 5658908; US 5681830; WO 9315062 .

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)	20690	(2R,5S)-1-allyl-2,5-dimethylpiperazine		C₉H₁₈N₂	详情	详情
(VI)	15859	Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid	7764-95-6	C₈H₁₅NO₄	详情	详情
(VII)	20693	(2R)-2-[allyl(tert-butoxycarbonyl)amino]propionic acid		C₁₁H₁₉NO₄	详情	详情
(VIII)	20694	methyl (2S)-2-aminopropanoate		C₄H₉NO₂	详情	详情
(IX)	20695	(2S)-2-([(2R)-2-[allyl(tert-butoxycarbonyl)amino]propanoyl]amino)propionic acid		C₁₄H₂₄N₂O₅	详情	详情
(X)	20696	(3S,6R)-1-allyl-3,6-dimethyl-2,5-piperazinedione		C₉H₁₄N₂O₂	详情	详情

Extended Information