反応式
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.CO.C(Cl)(Cl)Cl.CCCCCC.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:14][CH2:13][C@@H:11]2[O:10][C:9](=[O:15])[N:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[CH2:12]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1参加物
実験手順
A mixture of (R)-3-(3-fluorophenyl)-5-(hydroxymethyl)-2-oxooxazolidine (PREPARATION 14, 1.800 g, 8.52 mmol) in dry pyridine (10 ml) is cooled to 5° and then treated with p-toluenesulfonyl chloride (1.706 g, 8.95 mmol). The mixture is left at this temperature overnight. TLC with methanol/chloroform (5/95) or hexane/ethyl acetate (1/1) indicates the starting material is consumed. The reaction mixture is dumped into ice water (30 ml) and the resultant precipitate collected by vacuum filtration through a medium-porosity sintered glass funnel. The collected solids are thoroughly washed with cold water, dried under reduced pressure and recrystallized from ethyl acetate/hexane to give the title compound, mp 114-115°; [α]25D -62.6° (c 1.0, CH3CN); IR (mineral oil mull): 1751, 1617, 1591, 1499, 1415, 1362, 1227, 1202, 1191, 1172, 1093, 967 cm-1 ; NMR (CDCl3, 300 MHz) δ 7.78, 7.38, 7.36, 7.33, 7.16, 6.86, 4.84, 4.29, 4.24, 4.10, 3.88, 2.46; MS (m/z) 365, 149, 122, 91; HRMS (m/z) 365.0738 (calc'd for C17H16FNO5S: 365.0733).
後処理
- temperatureis cooled to 5°
- customis consumed
- filtrationthe resultant precipitate collected by vacuum filtration through a medium-porosity sintered glass funnel
- washThe collected solids are thoroughly washed with cold water
- customdried under reduced pressure
- customrecrystallized from ethyl acetate/hexane
出典と根拠
- ORDレコード
- ord-c10da0285a2c487ea8a38ee94015e1e4
- 出典データセット
- uspto-grants-1999_07
- 特許番号
- US05929248
関連ノート
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