Sodium Azide → (5R)-5-Azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-oxazolidin-2-one

温度

80 °C

(5R)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (13.6 g) was dissolved in dry N,N-dimethylformamide (110 ml). Sodium azide (3.53 g) was added, and the mixture was heated at 80° C. for 3.5 hours. The mixture was cooled, diluted with water (1.1 L) containing sodium bicarbonate (2 g), and extracted with ethyl acetate (2×800 ml). Combined organics were washed with water (2×300 ml), then brine, and dried over magnesium sulfate. The solution was evaporated to a small volume (˜100 ml), and insolubles filtered. The ethyl acetate soluble material was columned on silica (100 g), eluting with ethyl acetate. Product fractions were combined and evaporated to give a gum (10.0 g).

1. temperatureThe mixture was cooled
2. extractionextracted with ethyl acetate (2×800 ml)
3. washCombined organics were washed with water (2×300 ml)
4. dry with materialbrine, and dried over magnesium sulfate
5. customThe solution was evaporated to a small volume (˜100 ml), and insolubles
6. filtrationfiltered
7. washeluting with ethyl acetate
8. customevaporated

ORDレコード

ord-dc0121f5a4bf4f99b4f7302ab9237010

出典データセット

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06495551B1