benzyl (4R)-5-amino-4-[[(2S)-2-([2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]acetyl]oxy)propanoyl]amino]-5-oxopentanoate -Drug Synthesis Database

【结构式】

【分子编号】27131

【品名】benzyl (4R)-5-amino-4-[[(2S)-2-([2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]acetyl]oxy)propanoyl]amino]-5-oxopentanoate

【CA登记号】

【分子式】C₂₇H₂₉N₃O₉

【分子量】539.54208

【元素组成】C 60.11% H 5.42% N 7.79% O 26.69%

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：(VI)

The reaction of phthalimidocarboxylic acid ethyl ester (I) with 2-(2-aminoethoxy)ethanol (II) in THF gives N-[2-(2-hydroxyethoxy)ethyl]phthalimide (III), which is oxidized with CrO3/sulfuric acid in acetone yielding 2-(phthalimidoethoxy)acetic acid (IV). The condensation of (IV) with L-alanyl-D-isoglutamine benzyl ester (V) by means of phenylphosphoryl azide (DPPA) and triethylamine in DMF gives N-[2-(2-phthalimidoethoxy)acetyl]-L-alanyl-D-isoglutamine benzyl ester (VI), which is finally debenzylated by hydrogenation over Pd/C in acetic acid.

参考文献中间体

合成目标

【1】 Urleb, U.; et al.; Synthesis of phthalimido-desmuramylpeptide analogues as potential immunomodulating agents. Arch Pharm 1995, 328, 2, 113.
【2】 Pecar, S.; Sollner, M.; Urleb, U.; Kikelj, D.; Marc, G.; Krbavcic, A.; Kotnik, V.; Wraber-Herzog, B.; Simcic, S.; Ihan, A.; Klamfer, L.; Provsic, L.; Kopitar, Z.; Stalc, A. (LEK Pharmaceutical and Chemical Co.; University of Ljubljana); Novel N-acyldipeptides, processes for the preparation thereof and pharmaceutical compsns. containing the same. EP 0477912; JP 1994220087 .

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)	10283	ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide	22509-74-6	C₁₁H₉NO₄	详情	详情
(II)	19029	2-(2-aminoethoxy)-1-ethanol	929-06-6	C₄H₁₁NO₂	详情	详情
(III)	27128	2-[2-(2-hydroxyethoxy)ethyl]-1H-isoindole-1,3(2H)-dione		C₁₂H₁₃NO₄	详情	详情
(IV)	27129	2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]acetic acid		C₁₂H₁₁NO₅	详情	详情
(V)	27130	benzyl (4R)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate		C₁₅H₂₁N₃O₄	详情	详情
(VI)	27131	benzyl (4R)-5-amino-4-[[(2S)-2-([2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]acetyl]oxy)propanoyl]amino]-5-oxopentanoate		C₂₇H₂₉N₃O₉	详情	详情

Extended Information