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【结 构 式】

【分子编号】51561

【品名】(4S)-4-benzyl-3-(2-butylacryloyl)-5,5-dimethyl-1,3-oxazolidin-2-one

【CA登记号】

【 分 子 式 】C19H25NO3

【 分 子 量 】315.41244

【元素组成】C 72.35% H 7.99% N 4.44% O 15.22%

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)

The reaction of 2-butylmalonic acid (I) with piperidine and formaldehyde in refluxing ethanol gives 2-methylenehexanoic acid (II), which is condensed with the chiral auxiliary oxazolidine lithium salt (III) by means of pivaloyl chloride and TEA to yield the oxazolidide (IV). The addition of O-benzylhydroxylamine (V) to (IV) by means of Ts-OH proceeds with great stereospecificity, affording tosylate (VI), which is submitted to cleavage of the chiral auxiliary with LiOH in aqueous THF to provide the carboxylic acid (VII). The formylation of the benzylhydroxylamine group of (VII) with HCOO-Ac in THF gives the formamide (VIII), which is condensed with L-tert-leucine dimethylamide (IX) by means of HOAt and EDC in DMF to yield the pseudo dipeptide (X). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C in ethanol.

1 Pratt, L.M.; et al.; Asymmetric synthesis of BB-3497 - A potent peptide deformylase inhibitor. Bioorg Med Chem Lett 2001, 11, 19, 2585.
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) 45891 2-butylmalonic acid 534-59-8 C7H12O4 详情 详情
(II) 51559 2-butylacrylic acid C7H12O2 详情 详情
(III) 51560 [(4S)-4-benzyl-5,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]lithium C12H14LiNO2 详情 详情
(IV) 51561 (4S)-4-benzyl-3-(2-butylacryloyl)-5,5-dimethyl-1,3-oxazolidin-2-one C19H25NO3 详情 详情
(V) 14640 O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene 622-33-3 C7H9NO 详情 详情
(VI) 51562 (2R)-2-[[(4S)-4-benzyl-5,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl]-N-(benzyloxy)-1-hexanaminium 4-methylbenzenesulfonate C33H42N2O7S 详情 详情
(VII) 51563 (2R)-2-[[(benzyloxy)amino]methyl]hexanoic acid C14H21NO3 详情 详情
(VIII) 51564 (2R)-2-[[(benzyloxy)(formyl)amino]methyl]hexanoic acid C15H21NO4 详情 详情
(IX) 45886 (2S)-2-amino-N,N,3,3-tetramethylbutanamide C8H18N2O 详情 详情
(X) 45889 (2R)-2-[[(benzyloxy)(formyl)amino]methyl]-N-[(1S)-1-[(dimethylamino)carbonyl]-2,2-dimethylpropyl]hexanamide C23H37N3O4 详情 详情
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