methyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-hydroxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】55896

【品名】methyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-hydroxybenzoate

【CA登记号】

【分子式】C₂₁H₃₂N₂O₆

【分子量】408.49496

【元素组成】C 61.75% H 7.9% N 6.86% O 23.5%

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：(IV)

3-Iodo-L-tyrosine (I) was protected as the N-Boc derivative (II) and subsequently coupled to n-pentylamine yielding amide (III). Palladium-catalyzed carboxylation of the aryl iodide of (III) in the presence of MeOH afforded the methyl ester (IV). The phenolic hydroxyl group of (IV) was then alkylated with methyl bromoacetate under basic conditions to produce diester (V). Acidic Boc group cleavage in (V), followed by acylation of the resulting amine (VI) with N-Boc-L-phenylalanine (VII), generated the dipeptide derivative (VIII). Further deprotection of (VIII) with HCl in dioxane yielded amine (IX), which was finally coupled with succinic acid mono-methyl ester (X) to provide the title compound.

参考文献中间体

合成目标

【1】 Ogg, D.; Schostarez, H.J.; Stevens, F.C.; Bleasdale, J.E.; Larse, S.D.; May, P.D.; Liljebris, C.; Barf, T.; Palazuk, B.J.; O'Sullivan, T.J.; Synthesis and biological acrivity of a novel class of small molecular weight peptidomimetic competitive inhibitors of protein tyrosine phosphatase 1B. J Med Chem 2002, 45, 3, 598.
【2】 Bleasdale, J.; May, P.D.; Schostarez, H.J.; Barf, T.; Larsen, S.D.; Liljebris, C. (Pharmacia Corp.); Inhibitors of protein tyrosine phosphatase. WO 9911606 .

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)	55893	(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid		C₉H₁₀INO₃	详情	详情
(II)	55894	(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxy-3-iodophenyl)propanoic acid		C₁₄H₁₈INO₅	详情	详情
(III)	55895	tert-butyl (1S)-1-(4-hydroxy-3-iodobenzyl)-2-oxo-2-(pentylamino)ethylcarbamate		C₁₉H₂₉IN₂O₄	详情	详情
(IV)	55896	methyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-hydroxybenzoate		C₂₁H₃₂N₂O₆	详情	详情
(V)	55897	methyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)benzoate		C₂₄H₃₆N₂O₈	详情	详情
(VI)	55898	methyl 5-[(2S)-2-amino-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)benzoate		C₁₉H₂₈N₂O₆	详情	详情
(VII)	12874	(2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine	13734-34-4	C₁₄H₁₉NO₄	详情	详情
(VIII)	55899	methyl 5-[(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)benzoate		C₃₃H₄₅N₃O₉	详情	详情
(IX)	55900	methyl 5-[(2S)-2-{[(2S)-2-amino-3-phenylpropanoyl]amino}-3-oxo-3-(pentylamino)propyl]-2-(2-methoxy-2-oxoethoxy)benzoate		C₂₈H₃₇N₃O₇	详情	详情
(X)	55901	Methyl hydrogen succinate; Succinic acid monomethyl ester; Monomethyl succinate	3878-55-5	C₅H₈O₄	详情	详情

Extended Information