Potassium Cyanide → HCID 57208374, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.4 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-trimethylsilylethynylphenyl)-5-oxazolidinecarboxylate in 20 cm3 of ethanol is added dropwise, with stirring and at a temperature in the region of 20° C., a solution of 1.7 g of silver nitrate in a mixture of 2 cm3 of distilled water and 1 cm3 of ethanol. The reaction mixture is subsequently stirred for 2 hours at a temperature in the region of 20° C., followed by dropwise addition of a solution of 2.93 g of potassium cyanide in 3 cm3 of distilled water. Stirring is continued at a temperature in the region of 20° C. for 18 hours and the mixture is extracted with 3 times 50 cm3 of ethyl acetate. The organic phases are combined, washed with 3 times 5 cm3 of distilled water, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 0.55 g of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(4-ethynylphenyl)-5-oxazolidinecarboxylate is thus obtained, in the form of a brown oil which is converted to the corresponding acid under the conditions described in Example 2.

Provenance & Evidence