methyl (2S)-2-[[(2S,4R)-2-amino-4-methyloctanoyl](methyl)amino]propanoate -Drug Synthesis Database

【结构式】

【分子编号】26302

【品名】methyl (2S)-2-[[(2S,4R)-2-amino-4-methyloctanoyl](methyl)amino]propanoate

【CA登记号】

【分子式】C₁₄H₂₈N₂O₃

【分子量】272.388

【元素组成】C 61.73% H 10.36% N 10.28% O 17.62%

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：(XLI)

Coupling of N-Boc-5-propyl-L-leucine (X) with N-methyl-L-alanine methyl ester (XXXIX) in the presence of EDC and HOAt gave dipeptide (XL), which was deprotected with HCl in EtOAc to afford (XLI).

参考文献中间体

合成目标

【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(X)	26272	(2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-methyloctanoic acid	C₁₄H₂₇NO₄	详情	详情
(XXXIX)	26300	methyl (2S)-2-(methylamino)propanoate	C₅H₁₁NO₂	详情	详情
(XL)	26301	methyl (2S)-2-[[(2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-methyloctanoyl](methyl)amino]propanoate	C₁₉H₃₆N₂O₅	详情	详情
(XLI)	26302	methyl (2S)-2-[[(2S,4R)-2-amino-4-methyloctanoyl](methyl)amino]propanoate	C₁₄H₂₈N₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XLI)

Dipeptide (XLIV) was prepared by coupling N-Boc-L-leucine (XLII) with tryptophan derivative (XXII), followed by basic hydrolysis of the resulting dipeptide ester (XLIII). Dipeptides (XLIV) and (XLI) were then coupled in the presence of HATU to afford tetrapeptide (XLV), which was separated from minor amounts of a tryptophan-epimerized byproduct by semipreparative RP-HPLC. Tetrapeptide ester (XLV) was then hydrolyzed to acid (XLVI) with LiOH in aqueous tert-butanol.

参考文献中间体

合成目标

【1】 Boger, D.L.; et al.; Total synthesis of HUN-7293. J Am Chem Soc 1999, 121, 26, 6197.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXII)	26283	methyl (2S)-3-(1-methoxy-1H-indol-3-yl)-2-(methylamino)propanoate	C₁₄H₁₈N₂O₃	详情	详情
(XLI)	26302	methyl (2S)-2-[[(2S,4R)-2-amino-4-methyloctanoyl](methyl)amino]propanoate	C₁₄H₂₈N₂O₃	详情	详情
(XLII)	23663	(2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine	C₁₁H₂₁NO₄	详情	详情
(XLIII)	26303	methyl (2S)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoyl](methyl)amino]-3-(1-methoxy-1H-indol-3-yl)propanoate	C₂₅H₃₇N₃O₆	详情	详情
(XLIV)	26304	(2S)-2-[[(2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoyl](methyl)amino]-3-(1-methoxy-1H-indol-3-yl)propionic acid	C₂₄H₃₅N₃O₆	详情	详情
(XLV)	26305	methyl (6S,9S,12S,15S)-6-isobutyl-9-[(1-methoxy-1H-indol-3-yl)methyl]-2,2,8,14,15-pentamethyl-12-[(2R)-2-methylhexyl]-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate	C₃₈H₆₁N₅O₈	详情	详情
(XLVI)	26308	N-(Tert-butoxycarbonyl)-L-leucyl-(N-alpha-methyl-N-1-methoxy)-L-tryptophyl-L-(2-amino-4(R)-methyloctanoyl)-(N-methyl)-L-alanine; N-(Tert-butoxycarbonyl)-L-leucyl-(N-alpha-methyl-N-1-methoxy)-L-tryptophyl-L-(2-amino-4(R)-methyloctanoyl)-(N-methyl)-L-alanine	C₃₇H₅₉N₅O₈	详情	详情

Extended Information