tert-butyl (3S)-2,6-dioxopiperidinylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】27696

【品名】tert-butyl (3S)-2,6-dioxopiperidinylcarbamate

【CA登记号】

【分子式】C₁₀H₁₆N₂O₄

【分子量】228.24812

【元素组成】C 52.62% H 7.07% N 12.27% O 28.04%

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：(VII)

By deprotection of tripeptide (V) (hydrogenolysis of the benzyl group with H2 over Pd/C) followed by condensation with amino acid ester (XI) by means of diethyl cyanophosphonate (DECP) in DMF. The intermediates (V) and (XI) have been obtained as follows: 1.- The condensation of N-(tert-butoxycarbonyl)-L-valine (I) with L-leucine benzyl ester (II) by means of DCC, NMM and NHS gives the dipeptide (III), which is condensed with L-phenylalanine benzyl ester (IV) by first debenzylation and condensation as before yielding the desired tripeptide (V). 2.- The cyclization of N-(tert-butoxycarbonyl)-L-glutamine (VI) by means of DCC and NHS gives the glutarimide (VII), which is partially reduced with NaBH4 to the cyclic Boc-glutaminal (VIII). The condensation of (VIII) with the phosphonate (IX) by means of NaH in THF affords the unsaturated protected aminoester (X), which is finally deprotected with trifluoroacetic acid in dichloromethane providing the desired amino acid ester (XI).

参考文献中间体

合成目标

【1】 Shepherd, T.A.; Furness, K.; Venkatraman, S.; Wang, Q.M.; Aubé, J.; Nimkar, S.; Kong, J.; Hanzlik, R.P.; Synthesis and evaluation of peptidyl Michael acceptors that inactivate human rhinovirus 3C protease and inhibit virus replication. J Med Chem 1998, 41, 14, 2579.

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)	19733	(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid		C₁₀H₁₉NO₄	详情	详情
(II)	27691	benzyl (2S)-2-amino-5-methylhexanoate		C₁₄H₂₁NO₂	详情	详情
(III)	27692	benzyl (2S)-2-([(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]amino)-5-methylhexanoate		C₂₄H₃₈N₂O₅	详情	详情
(IV)	27693	benzyl (2S)-2-amino-3-phenylpropanoate；L-phenylalanine benzyl ester		C₁₆H₁₇NO₂	详情	详情
(V)	27694	benzyl (6S,9S,12S)-12-benzyl-9-isopentyl-6-isopropyl-2,2-dimethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate		C₃₃H₄₇N₃O₆	详情	详情
(VI)	27695	(2S)-6-amino-2-[(tert-butoxycarbonyl)amino]-6-oxohexanoic acid		C₁₁H₂₀N₂O₅	详情	详情
(VII)	27696	tert-butyl (3S)-2,6-dioxopiperidinylcarbamate		C₁₀H₁₆N₂O₄	详情	详情
(VIII)	27697	tert-butyl (3S)-2-hydroxy-6-oxopiperidinylcarbamate		C₁₀H₁₈N₂O₄	详情	详情
(IX)	27698	methyl 2-(diethoxyphosphoryl)acetate	1067-74-9	C₇H₁₅O₅P	详情	详情
(X)	27699	methyl (E,4S)-8-amino-4-[(tert-butoxycarbonyl)amino]-8-oxo-2-octenoate		C₁₄H₂₄N₂O₅	详情	详情
(XI)	27700	methyl (E,4S)-4,8-diamino-8-oxo-2-octenoate		C₉H₁₆N₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

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