(3S)-3-amino-2,6-piperidinedione -Drug Synthesis Database

【结构式】

【分子编号】48171

【品名】(3S)-3-amino-2,6-piperidinedione

【CA登记号】

【分子式】C₅H₈N₂O₂

【分子量】128.1308

【元素组成】C 46.87% H 6.29% N 21.86% O 24.97%

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：(III)

The cyclization of N-(benzyloxycarbonyl)-L-glutamine (I) by means of CDI in THF gives the piperidinedione (II), which is deprotected by means of HBr in AcOH to yield 3(S)-aminopiperidine-2,6-dione (III).The condensation of (III) with 3-nitrophthalic anhydride (IV) in hot DMF/AcOH affords 3(S)-phthalimido-piperidine-2,6-dione (V), which is finally reduced with H2 over Pd/C in dioxane/methanol to provide the target thalidomide derivative.

参考文献中间体

合成目标

【1】 D'Amato, R.J.; Shah, J.H.; Hunsucker, K.A.; Pribluda, V.; Treston, A.; Rougas, J.; Conner, B.P.; Swartz, G.M. (Children's Medical Center Corp.); Synthesis of 3-amino-thalidomide and its enantiomers. WO 0264083 .

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)	26289	(2S)-5-amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid		C₁₃H₁₆N₂O₅	详情	详情
(II)	64520	benzyl (3S)-2,6-dioxopiperidinylcarbamate		C₁₃H₁₄N₂O₄	详情	详情
(III)	48171	(3S)-3-amino-2,6-piperidinedione		C₅H₈N₂O₂	详情	详情
(IV)	46407	4-nitro-2-benzofuran-1,3-dione；3-nitrophthalic anhydride	641-70-3	C₈H₃NO₅	详情	详情
(V)	34429	2-[(3S)-2,6-dioxopiperidinyl]-4-nitro-1H-isoindole-1,3(2H)-dione		C₁₃H₉N₃O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

In an alternative synthesis, (S)-3-(tert-butoxycarbonylamino)glutarimide (IV) was deprotected by means of trifluoroacetic acid to yield the aminoglutarimide (V). BOP-mediated coupling of (V) with 10-undecenoic acid (VI) then gave the target amide.

参考文献中间体

合成目标

【1】 Fox, D.J.; Grainger, D.J.; Reckless, J.; Warren, S.G.; Design, synthesis, and preliminary pharmacological evaluation of N-acyl-3-aminoglutarimides as broad-spectrum chemokine inhibitors in vitro and anti-inflammatory agents in vivo. J Med Chem 2002, 45, 2, 360.
【2】 Grainger, D.J.; Tatalick, L.M. (NeoRx Corp.); Cpds. and methods to inhibit or augment an inflammatory response. WO 0042071 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	27696	tert-butyl (3S)-2,6-dioxopiperidinylcarbamate		C₁₀H₁₆N₂O₄	详情	详情
(V)	48171	(3S)-3-amino-2,6-piperidinedione		C₅H₈N₂O₂	详情	详情
(VI)	48172	Kyselina Undecylenova; n-Undecylenic acid; 10-Henedecenoic acid; Undec-10-enoic acid; 10-Hendecenoic acid; Undecyl-10-enic acid; 10-Hendecenoic; 9-Undecylenic acid; 10-Undecylenic acid; 10-undecenoic acid	112-38-9	C₁₁H₂₀O₂	详情	详情

Extended Information