tert-butyl (1S)-1-[[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]carbonyl]-2-methylpropylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】27097

【品名】tert-butyl (1S)-1-[[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]carbonyl]-2-methylpropylcarbamate

【CA登记号】

【分子式】C₁₄H₂₀N₂O₆

【分子量】312.32268

【元素组成】C 53.84% H 6.45% N 8.97% O 30.74%

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：(I)

N-Boc-L-Valine N-hydroxysuccinimidyl ester (I) was coupled to L-proline benzyl ester (II), and the resulting Boc dipeptide (III) was subsequently deprotected with trifluoroacetic acid in CH2Cl2 to afford (IV). This was condensed with N-Boc-L-aspartic acid gamma-benzyl 1-N-hydroxysuccinimidyl diester (V) to give (VI). After Boc deprotection of (VI) with trifluoroacetic acid, tripeptide (VII) was coupled with N-Boc-L-leucine N-hydroxysuccinimidyl ester (VIII) to yield tetrapeptide (IX). Further Boc deprotection of (IX) with trifluoroacetic acid furnished peptide intermediate (X).

参考文献中间体

合成目标

【1】 Ateeq, H.S.; Lin, K.-C.; Hsiung, S.H.; et al.; Selective, tight-binding inhibitors of integrin alpha4beta1 that inhibit allergic airway responses. J Med Chem 1999, 42, 5, 920.
【2】 Lin, K.-C.; Adams, S.P.; Castro, A.C.; Zimmerman, C.N.; Cuervo, J.H.; Lee, W.-C.; Hammond, C.E.; Carter, M.B.; Almquist, R.G.; Ensinger, C.L. (Biogen, Inc.); Cell adhesion inhibitor. EP 0842196; JP 1999511124; WO 9703094 .

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)	27097	tert-butyl (1S)-1-[[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]carbonyl]-2-methylpropylcarbamate		C₁₄H₂₀N₂O₆	详情	详情
(II)	20930	benzyl (2S)-2-pyrrolidinecarboxylate	16652-71-4	C₁₂H₁₅NO₂	详情	详情
(III)	27098	benzyl (2S)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]-2-pyrrolidinecarboxylate		C₂₂H₃₂N₂O₅	详情	详情
(IV)	27099	benzyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]-2-pyrrolidinecarboxylate		C₁₇H₂₄N₂O₃	详情	详情
(V)	27100	benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]-4-oxobutanoate		C₂₀H₂₂N₂O₈	详情	详情
(VI)	27101	benzyl (2S)-1-[(2S)-2-([(2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoyl]amino)-3-methylbutanoyl]-2-pyrrolidinecarboxylate		C₃₃H₄₃N₃O₈	详情	详情
(VII)	27102	benzyl (2S)-1-((2S)-2-[[(2S)-2-amino-4-(benzyloxy)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate		C₂₈H₃₅N₃O₆	详情	详情
(VIII)	27103	tert-butyl (1S)-1-[[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]carbonyl]-3-methylbutylcarbamate		C₁₅H₂₂N₂O₆	详情	详情
(IX)	27104	benzyl (2S)-1-[(2S,5S,8S)-5-[2-(benzyloxy)-2-oxoethyl]-8-isobutyl-2-isopropyl-12,12-dimethyl-4,7,10-trioxo-11-oxa-3,6,9-triazatridec-1-anoyl]-2-pyrrolidinecarboxylate		C₃₉H₅₄N₄O₉	详情	详情
(X)	27105	benzyl (2S)-1-((2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-(benzyloxy)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate		C₃₄H₄₆N₄O₇	详情	详情

Extended Information