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【结 构 式】

【分子编号】28264

【品名】tert-butyl 4-amino-2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)butanoate

【CA登记号】

【 分 子 式 】C24H38N2O3

【 分 子 量 】402.5774

【元素组成】C 71.6% H 9.51% N 6.96% O 11.92%

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:(XII)

The condensation of gamma-butyrolactone (I) with phenethyl amine (II) at high temperatures afforded phenethylpyrrolidinone (III). This was alkylated with isobutyl iodide (IV) in the presence of lithium diisopropylamide in cold THF yielding the 3-isobutyl pyrrolidinone (V), and further alkylated with tert-butyl bromoacetate (VI) to give (VII). Subsequent alkylation of (VII) at the alpha-position of carboxylate group with allyl bromide provided (VIII). Ozonolysis of the double bond of (VIII), followed by reductive treatment with NaBH4 produced alcohol (IX), which was coupled with dibenzyl iminodicarboxylate (X) under Mitsunobu conditions giving (XI). The biscarbamate (XI) was deprotected by hydrogenolysis over Pd/C, and the resulting primary amine (XII) was condensed with 3,4-difluorobenzoyl chloride (XIII) to furnish amide (XIV). Then, trifluoroacetic acid-promoted cleavage of the tert-butyl ester of (XIV) provided the corresponding carboxylic acid, which was finally coupled with hydroxylamine by means of EDC and HOBt to afford the target hydroxamic acid

1 Jacobsen, E.J. (Pharmacia & Upjohn AB); Hydroxamic acid derivs. for use with the treatment of diseases related to connective tissue degradation. EP 0898562; JP 2000506163; US 5712300; WO 9732846 .
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) 20576 dihydro-2(3H)-furanone 96-48-0 C4H6O2 详情 详情
(II) 18333 Phenethylamine; 2-Phenyl-1-ethanamine 64-04-0 C8H11N 详情 详情
(III) 28259 1-phenethyl-2-pyrrolidinone C12H15NO 详情 详情
(IV) 18168 1-iodo-2-methylpropane 513-38-2 C4H9I 详情 详情
(V) 28267 3-isobutyl-1-phenethyl-2-pyrrolidinone C16H23NO 详情 详情
(VI) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(VII) 28260 tert-butyl 2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)acetate C22H33NO3 详情 详情
(VIII) 28261 tert-butyl 2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)-4-pentenoate C25H37NO3 详情 详情
(IX) 28268 tert-butyl 4-hydroxy-2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)butanoate C24H37NO4 详情 详情
(X) 28262 1-[[([[(benzyloxy)carbonyl]amino]carbonyl)oxy]methyl]benzene C16H15NO4 详情 详情
(XI) 28263 tert-butyl 4-[bis[(benzyloxy)carbonyl]amino]-2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)butanoate C40H50N2O7 详情 详情
(XII) 28264 tert-butyl 4-amino-2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)butanoate C24H38N2O3 详情 详情
(XIII) 28265 3,4-difluorobenzoyl chloride 76903-88-3 C7H3ClF2O 详情 详情
(XIV) 28266 tert-butyl 4-[(3,4-difluorobenzoyl)amino]-2-(3-isobutyl-2-oxo-1-phenethyl-3-pyrrolidinyl)butanoate C31H40F2N2O4 详情 详情
Extended Information