Reaktion #8242

Reaktionsgleichung

5(R)—(N-(2,2,2-Trichloroethyloxycarbonyl)-isoxazol-3-ylaminomethyl)-3-(4-imidazol-1-yl-3-fluorophenyl)oxazolidin-2-one

→

desired product

Ausbeute 41.8%

5(S)-Isoxazol-3-ylaminomethyl-3-(4-imidazol-1-yl-3-fluorophenyl)-oxazolidin-2-one

Ausbeute 41.8%

Lösungsmittel

acetic acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 1 hour
3. 3
   FiltrationThe mixture was filtered through celite
4. 4
   Waschenthe filter pad washed well with a mixture of acetic acid and water (5:1)
5. 5
   SonstigeThe filtrates were evaporated
6. 6
   Sonstigethe residue partitioned between hydrochloric acid (0.5M, 200 ml) and dichloromethane (150 ml)
7. 7
   WaschenThe aqueous phase was washed with dichloromethane (100 ml)
8. 8
   Extraktionre-extracted with dichloromethane (2×150 ml)
9. 9
   Trocknendried (magnesium sulfate)
10. 10
    Sonstigeevaporated
11. 11
    SonstigeRecrystallisation from isopropanol (40 ml)

Vorschrift

5(R)—(N-(2,2,2-Trichloroethyloxycarbonyl)-isoxazol-3-ylaminomethyl)-3-(4-imidazol-1-yl-3-fluorophenyl)oxazolidin-2-one (crude, 1.7 g, ˜2.5 mM), was stirred in a mixture of acetic acid (40 ml) and water (18 ml) under nitrogen at ambient temperature. Zinc dust (824 mg, 12.5 mM) was added, the mixture stirred 20 minutes, a further portion (200 mg) of zinc added, and stirring continued for 1 hour. The mixture was filtered through celite, and the filter pad washed well with a mixture of acetic acid and water (5:1). The filtrates were evaporated, and the residue partitioned between hydrochloric acid (0.5M, 200 ml) and dichloromethane (150 ml). The aqueous phase was washed with dichloromethane (100 ml), then made basic with the minimum quantity of concentrated ammonia solution, re-extracted with dichloromethane (2×150 ml), dried (magnesium sulfate), and evaporated. Recrystallisation from isopropanol (40 ml) gave the desired product (470 mg).

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