Acetone → 4-[5-(Hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]benzene-1-sulfonyl azide

Participants

Reaction Conditions

Reaction Steps

A solution of 10 g sodium azide in 20 ml water was added to 200 ml reagent grade acetone and then cooled to -5° C. A 19 g portion of dl-4-[5-(trifluoroacetoxymethyl)-2-oxooxazolidin-3-yl]benzenesulfonyl chloride (prepared as in Example 1) was added to the solution while maintaining the temperature of the mixture below 0° C. After stirring the mixture for one hour, it was allowed to stand overnight. The acetone was removed under reduced pressure, water was added and the product was filtered and washed with water to yield 12.8 g, m.p. 108°-110° C. This product was stirred with 250 ml acetonitrile at 25° C. and filtered to remove some insoluble material. The acetonitrile was concentrated and the crystallized product filtered to yield 12.3 g. This product was recrystallized from ethyl acetae to yield 6.0 g of the title compound, m.p. 112°-113° C.

Provenance & Evidence