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【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.

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