Sodium Carbonate → HCID 11681550, compound

Participants

Reaction Conditions

Reaction Steps

(4S,5R)-2,2-Dimethyl-4-phenyl-5-vinyl-oxazolidine-3-carboxylic acid t-butyl ester is dissolved in a polar solvent. Carbon tetrachloride and water are added, followed by the addition of a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, or sodium bicarbonate, at a temperature in the range of about 10-50° C. The reaction mixture is stirred for about 10 to 20 minutes and an alkali metal periodate, such as sodium metaperiodate, is added in small portions to the reaction mixture, such as over a period of about 20 to 40 minutes. A ruthenium salt catalyst, such as ruthenium trichloride, is added to the reaction mixture at a temperature in the range of about 20-40° C. and stirred to reaction completion, such as for about 30-40 hours. The reaction mass is filtered and the filtrate is washed with ethyl acetate, then the aqueous layer is cooled to about 10-15° C. and acidified with 10% aqueous hydrochloric acid to pH 2-3. The aqueous layer is extracted with ethyl acetate, then the organic layer is washed with a 2% aqueous Na2S2O3 solution and washed with brine solution. The organic layer is concentrated at about 50° C. under vacuum to get a thick semi-solid. The solid is triturated with petroleum ether and filtered to get the desired white solid (4S,5R)-5-carboxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid t-butyl ester (I).

Provenance & Evidence