4-Toluenesulfonyl chloride → (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

HRID 583565

Reaktionsgleichung

Reaktionsgleichung von HRID 583565
[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

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 11229590(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-oneHCID 21226206Ethyl acetate hexaneHCID 21584188Chloroform methanol

Produkt 1

HCID 54408340(R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureis cooled to 5°
  2. customis consumed
  3. filtrationthe resultant precipitate collected by vacuum filtration through a medium-porosity sintered glass funnel
  4. washThe collected solids are thoroughly washed with cold water
  5. customdried under reduced pressure
  6. customrecrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c10da0285a2c487ea8a38ee94015e1e4
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929248

Verknüpfte Notizen

Wird geladen…