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【结 构 式】

【分子编号】57009

【品名】tert-butyl (2S,3R)-2,5-dimethyl-3-({[(1S)-2-(methylamino)-2-oxo-1-phenylethyl]amino}carbonyl)hexanoate

【CA登记号】

【 分 子 式 】C22H34N2O4

【 分 子 量 】390.52304

【元素组成】C 67.66% H 8.78% N 7.17% O 16.39%

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:(VIII)

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
Extended Information