Reaktion #8280

Reaktionsgleichung

2-aminooxazole

n-BuLi

5(R)-methylsulfonyloxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one

→

title compound

Ausbeute 4.6%

5(S)Oxazol-2-ylaminomethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4 yl)phenyl)oxazolidin-2-one

Ausbeute 4.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto come to room temperature
2. 2
   Temperaturrefluxed for 24 h
3. 3
   SonstigeThe reaction was quenched with ammonium chloride solution (10% w/v, 30 ml)
4. 4
   Extraktionextracting the mixture with chloroform (3×50 ml)
5. 5
   TrocknenThe extracts were dried (magnesium sulfate)
6. 6
   Einengenconcentrated by rotary evaporation
7. 7
   Sonstigechromatographed by MPLC (Merck 9385 silica, 3–10% gradient methanol/dichloromethane eluent)
8. 8
   Einengenconcentrated
9. 9
   Sonstigetriturated with diethyl ether

Vorschrift

To a stirred partial solution of 2-aminooxazole (169 mg, 2.0 mmol) in dry THF (10 ml), cooled to −78° C., under argon, was added slowly n-BuLi (1.33M, 1.5 ml, 2.0 mmol), followed after 1 h by 5(R)-methylsulfonyloxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (see Example 41; 371 mg, 11.0 mol) suspended in dry THF (20 ml). The reaction was allowed to come to room temperature and then refluxed for 24 h. The reaction was quenched with ammonium chloride solution (10% w/v, 30 ml), extracting the mixture with chloroform (3×50 ml). The extracts were dried (magnesium sulfate), concentrated by rotary evaporation chromatographed by MPLC (Merck 9385 silica, 3–10% gradient methanol/dichloromethane eluent) and the pure fractions combined, concentrated and triturated with diethyl ether to give the title compound (25 mg, 4.6%).

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