Isobutoxycarbinyl-D-seryl-L-alanine 1-[2-ethoxy-1-(N2-nitroamidino)piperidin-3(S)-ylamide -Drug Synthesis Database

【结构式】

【分子编号】29389

【品名】Isobutoxycarbinyl-D-seryl-L-alanine 1-[2-ethoxy-1-(N2-nitroamidino)piperidin-3(S)-ylamide

【CA登记号】

【分子式】C₁₉H₃₅N₇O₈

【分子量】489.52928

【元素组成】C 46.62% H 7.21% N 20.03% O 26.15%

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：(XIX)

The compound was also prepared by solution-phase synthesis. Treatment of O-tert-butyl-D-serine (XIII) with isobutyl chloroformate (XII) produced carbamate (XIV). Subsequent coupling of (XIV) with L-alanine tert-butyl ester (XV) by means of EDC and HOBt yielded the protected dipeptide (XVI). Deprotection of both tert-butyl groups of (XVI) with trifluoroacetic acid produced dipeptide (XVII), which was coupled to nitro-L-arginine ethyl aminal (XVIII) to furnish tripeptide (XIX). Hydrogenolysis of the nitro group of (XIX) over Pd/C gave (XX). The ethyl acetal of (XX) was finally hydrolyzed in 3M HCl to yield the title compound.

参考文献中间体

合成目标

【1】 Cohen, C.R.; Weinhouse, M.I.; Roberts, C.; et al.; Synthesis and biological activity of transition-state urokinase inhibitors. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 090.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	13423	1-[(Chlorocarbonyl)oxy]-2-methylpropane; Isobutyl chloroformate;isobutyl carbonochloridate	543-27-1	C₅H₉ClO₂	详情	详情
(XIII)	29383	(2R)-2-amino-3-(tert-butoxy)propionic acid		C₇H₁₅NO₃	详情	详情
(XIV)	29384	(2R)-3-(tert-butoxy)-2-[(isobutoxycarbonyl)amino]propionic acid		C₁₂H₂₃NO₅	详情	详情
(XV)	29385	tert-butyl (2S)-2-aminopropanoate		C₇H₁₅NO₂	详情	详情
(XVI)	29386	tert-butyl (2S)-2-([(2R)-3-(tert-butoxy)-2-[(isobutoxycarbonyl)amino]propanoyl]amino)propanoate		C₁₉H₃₆N₂O₆	详情	详情
(XVII)	29387	(2S)-2-([(2R)-3-hydroxy-2-[(isobutoxycarbonyl)amino]propanoyl]amino)propionic acid		C₁₁H₂₀N₂O₆	详情	详情
(XVIII)	29388	3(S)-Amino-2-ethoxy-N2-nitropiperidine-1-carboxamidine		C₈H₁₇N₅O₃	详情	详情
(XIX)	29389	Isobutoxycarbinyl-D-seryl-L-alanine 1-[2-ethoxy-1-(N2-nitroamidino)piperidin-3(S)-ylamide		C₁₉H₃₅N₇O₈	详情	详情
(XX)	29390	isobutyl (1R)-2-[[(1S)-2-([(3S)-1-[amino(imino)methyl]-2-ethoxypiperidinyl]amino)-1-methyl-2-oxoethyl]amino]-1-(hydroxymethyl)-2-oxoethylcarbamate		C₁₉H₃₆N₆O₆	详情	详情

Extended Information