Sodium Azide → (5R)-5-(Azidomethyl)-3-(3-fluorophenyl)-2-oxazolidinone

HRID 583566

Reaktionsgleichung

Reaktionsgleichung von HRID 583566
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:17][C:16](=[O:18])[N:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[CH2:14]2)(=O)=O)=CC=1.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[F:25][C:21]1[CH:20]=[C:19]([N:15]2[CH2:14][C@H:13]([CH2:12][N:26]=[N+:27]=[N-:28])[O:17][C:16]2=[O:18])[CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 54408340(R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

Produkt 1

HCID 11550435(5R)-5-(Azidomethyl)-3-(3-fluorophenyl)-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of (R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate (PREPARATION 15, 2.340 g, 6.40 mmol) in dry DMF (60 ml) is treated with solid sodium azide (3.331 g, 51.23 mmmol) at 20-25°. The resultant slurry is warmed to 65° for 4.5 hr and then cooled to 20-25° and left overnight. The reaction mixture is then diluted with ethyl acetate and water, transferred to a separatory funnel, and extracted with ethyl acetate. The combined ethyl acetate extracts are washed thoroughly with water, and then dried (sodium sulfate), filtered and concentrated under reduced pressure to give the title compound, mp 81-82°; [α]25D -136.5° (c 0.9, CHCl3); IR (mineral oil mull): 2115, 1736, 1614, 1591, 1586, 1497, 1422, 1233, 1199, 1081, 1049 cm-1 ; NMR (CDCl3, 300 MHz) δ 7.45, 7.34, 7.23, 6.86, 4.81, 4.09, 3.86, 3.72 and 3.60; MS (m/z) 236 (59.0, M+), 179, 136, 122, 109, 95, 75; HRMS (m/z) 236.0708 (calc'd for C10H9FN4O2 : 236.0709).

Aufarbeitung

  1. temperatureThe resultant slurry is warmed to 65° for 4.5 hr
  2. temperaturecooled to 20-25°
  3. customtransferred to a separatory funnel
  4. extractionextracted with ethyl acetate
  5. washThe combined ethyl acetate extracts are washed thoroughly with water
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-649d99a9f1ee4265b0761a9edfcd6e90
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929248

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