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【结 构 式】

【分子编号】12868

【品名】(4S)-4-Isopropyl-3-[3-(1-naphthyl)propanoyl]-1,3-oxazolidin-2-one

【CA登记号】

【 分 子 式 】C19H21NO3

【 分 子 量 】311.38068

【元素组成】C 73.29% H 6.8% N 4.5% O 15.41%

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:(V)

The starting product (I) is obtained as follows: The acylation of 4(S)-isopropyloxazolidin-2-one (IV) with 3-(1-naphthyl)propionyl chloride (III) by means of butyllithium in THF-hexane yields 4(S)-isopropyl-3-[3-(1-naphthyl)propionyl]oxazolidin-2-one (V), which is condensed with benzyl bromoacetate (VI) by means of lithium diisopropylamide in THF to afford 3-[3-(benzyloxycarbonyl)-2(R)-(1-naphthylmethyl)propionyl]-4(S)-isoprop yloxazolidin-2-one (VII). The hydrogenolysis of (VII) with H2 over Pd/C in ethanol gives the carboxylic acid (VIII), which is condensed with morpholine (IX) by means of triethylamine and diethylphosphoryl cyanide in THF yielding 4(S)-isopropyl-3-[3-(morpholinocarbonyl)-2(R)-(1-naphthylmethyl)propion yl]oxazolidin-2-one (X). Finally, this compound is hydrolyzed with LiOH in THF - water to afford the acid (I).

1 Nishi, T.; Nagahori, H.; Saito, F.; et al.; Syntheses and biological activities of renin inhibitors containing statine analogues. Chem Pharm Bull 1990, 38, 1, 103-9.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 12866 3-(1-Naphthyl)propanoyl chloride C13H11ClO 详情 详情
(IV) 12867 (4S)-4-Isopropyl-1,3-oxazolidin-2-one; (R)-4-Isopropyl-2-oxazolidinone 17016-83-0 C6H11NO2 详情 详情
(V) 12868 (4S)-4-Isopropyl-3-[3-(1-naphthyl)propanoyl]-1,3-oxazolidin-2-one C19H21NO3 详情 详情
(VI) 12869 benzyl 2-bromoacetate 5437-45-6 C9H9BrO2 详情 详情
(VII) 12870 benzyl (3R)-4-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-3-(1-naphthylmethyl)-4-oxobutanoate C28H29NO5 详情 详情
(VIII) 12871 (3R)-4-[(4S)-4-Isopropyl-2-oxo-1,3-oxazolidin-3-yl]-3-(1-naphthylmethyl)-4-oxobutyric acid C21H23NO5 详情 详情
(IX) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(X) 12873 Boc-L-phenylalanine;N-[(1,1-Dimethylethoxy)carbonyl]-L-phenylalanine;N-(tert-Butoxycarbonyl)-L-phenylalanine;(R)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid;N-Boc-Lhomophenylalanine;(2R)-1-[(4S)-4-Isopropyl-2-oxo-1,3-oxazolidin-3-yl]-4-(4-morpholinyl)-2-(1-naphthylmethyl)-1,4-butanedione C25H30N2O5 详情 详情
Extended Information