【结 构 式】 |
【分子编号】57005 【品名】benzyl (2S,3R)-3-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-2,5-dimethylhexanoate 【CA登记号】 |
【 分 子 式 】C26H31NO5 【 分 子 量 】437.53588 【元素组成】C 71.37% H 7.14% N 3.2% O 18.28% |
合成路线1
该中间体在本合成路线中的序号:(III)An alternative, stereoselective synthesis has been reported. The alkylation of the chiral N-acyl oxazolidinone (I) with benzyl L-2-[(trifluoromethylsulfonyl)oxy]propionate (II) leads to the succinic acid derivative (III). After hydrogenolysis of the benzyl ester group of (III), the resultant carboxylic acid (IV) is esterified with isobutylene and H2SO4 to afford the tert-butyl ester (V). Removal of the chiral auxiliary group of (V) is then effected by hydrolysis with lithium peroxide, yielding acid (VI). Subsequent coupling of (VI) with L-phenylglycine-N-methylamide (VII) provides diamide (VIII). Acidic tert-butyl ester cleavage in (VIII) gives acid (IX), which is condensed with O-benzyl hydroxylamine to furnish hydroxamate (X). The O-benzyl group of (X) is finally removed by catalytic hydrogenolysis over Pd/C.
【1】 Hirayama, R.; et al.; Synthesis and biological evaluation of orally active matrix metalloproteinase inhibitors. Bioorg Med Chem 1997, 5, 4, 765. |
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) | 25391 | (4S)-4-benzyl-3-(4-methylpentanoyl)-1,3-oxazolidin-2-one | C16H21NO3 | 详情 | 详情 | |
(II) | 43504 | benzyl (2S)-2-[[(trifluoromethyl)sulfonyl]oxy]propanoate | C11H11F3O5S | 详情 | 详情 | |
(III) | 57005 | benzyl (2S,3R)-3-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-2,5-dimethylhexanoate | C26H31NO5 | 详情 | 详情 | |
(IV) | 57006 | (2S,3R)-3-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-2,5-dimethylhexanoic acid | C19H25NO5 | 详情 | 详情 | |
(V) | 57007 | tert-butyl (2S,3R)-3-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-2,5-dimethylhexanoate | C23H33NO5 | 详情 | 详情 | |
(VI) | 57008 | (2R)-2-[(1S)-2-(tert-butoxy)-1-methyl-2-oxoethyl]-4-methylpentanoic acid | C13H24O4 | 详情 | 详情 | |
(VII) | 57000 | (2S)-2-amino-N-methyl-2-phenylethanamide | C9H12N2O | 详情 | 详情 | |
(VIII) | 57009 | tert-butyl (2S,3R)-2,5-dimethyl-3-({[(1S)-2-(methylamino)-2-oxo-1-phenylethyl]amino}carbonyl)hexanoate | C22H34N2O4 | 详情 | 详情 | |
(IX) | 57010 | (2S,3R)-2,5-dimethyl-3-({[(1S)-2-(methylamino)-2-oxo-1-phenylethyl]amino}carbonyl)hexanoic acid | C18H26N2O4 | 详情 | 详情 | |
(X) | 57004 | (2R)-N~4~-(benzyloxy)-2-isobutyl-N~1~-[(1S)-2-(methylamino)-2-oxo-1-phenylethyl]-3-methylenebutanediamide | C25H31N3O4 | 详情 | 详情 |