(2S)-2-amino-N-[(1S)-2-hydroxy-1-isobutylhexyl]-3-(1H-imidazol-5-yl)propanamide -Drug Synthesis Database

【结构式】

【分子编号】42807

【品名】(2S)-2-amino-N-[(1S)-2-hydroxy-1-isobutylhexyl]-3-(1H-imidazol-5-yl)propanamide

【CA登记号】

【分子式】C₁₆H₃₀N₄O₂

【分子量】310.43996

【元素组成】C 61.9% H 9.74% N 18.05% O 10.31%

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：(VIII)

Butylmagnesium bromide (II) was added to the Weinreb amide of Boc-L-leucine (I), yielding ketone (III), which was further reduced with NaBH4 to give alcohol (IV) as a diastereomeric mixture. The Boc protecting group of (IV) was removed employing trifluoroacetic acid in CH2Cl2, and the resulting amino alcohol (V) was coupled with N-Boc-L-histidine (VI) by means of BOP reagent to afford amide (VII). Deprotection of the Boc group of (VII) with trifluoroacetic acid then furnished the target C-terminal fragment (VIII).

参考文献中间体

合成目标

【1】 Cristau, M.; et al.; Synthesis and biological evaluation of bombesin constrained analogues. J Med Chem 2000, 43, 12, 2356.

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)	40395	tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-3-methylbutylcarbamate		C₁₃H₂₆N₂O₄	详情	详情
(II)	42802	bromo(butyl)magnesium	693-03-8	C₄H₉BrMg	详情	详情
(III)	42803	tert-butyl (1S)-1-isobutyl-2-oxohexylcarbamate		C₁₅H₂₉NO₃	详情	详情
(IV)	42804	tert-butyl (1S)-2-hydroxy-1-isobutylhexylcarbamate		C₁₅H₃₁NO₃	详情	详情
(V)	42805	(4S)-4-amino-2-methyl-5-nonanol		C₁₀H₂₃NO	详情	详情
(VI)	42808	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-imidazol-5-yl)propionic acid	17791-52-5	C₁₁H₁₇N₃O₄	详情	详情
(VII)	42806	tert-butyl (1S)-2-[[(1S)-2-hydroxy-1-isobutylhexyl]amino]-1-(1H-imidazol-5-ylmethyl)-2-oxoethylcarbamate		C₂₁H₃₈N₄O₄	详情	详情
(VIII)	42807	(2S)-2-amino-N-[(1S)-2-hydroxy-1-isobutylhexyl]-3-(1H-imidazol-5-yl)propanamide		C₁₆H₃₀N₄O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

Deprotection of the benzyl ester group of the N-terminal fragment (XX) by hydrogenolysis provided carboxylic acid (XXI). This was finally coupled with the C-terminal fragment (VIII) employing BOP reagent to furnish the title peptide derivative.

参考文献中间体

合成目标

【1】 Cristau, M.; et al.; Synthesis and biological evaluation of bombesin constrained analogues. J Med Chem 2000, 43, 12, 2356.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VIII)	42807	(2S)-2-amino-N-[(1S)-2-hydroxy-1-isobutylhexyl]-3-(1H-imidazol-5-yl)propanamide	C₁₆H₃₀N₄O₂	详情	详情
(XX)	42815	benzyl 2-[(3S)-3-[((2S)-2-[[(2S)-2-[((2S)-5-amino-2-[[3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl)amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl)amino]-2-oxoazepanyl]acetate	C₄₃H₅₁N₇O₉	详情	详情
(XXI)	42816	2-[(3S)-3-[((2S)-2-[[(2S)-2-[((2S)-5-amino-2-[[3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl)amino]-3-(1H-indol-3-yl)propanoyl]amino]propanoyl)amino]-2-oxoazepanyl]acetic acid	C₃₆H₄₅N₇O₉	详情	详情

Extended Information