Methanol → HCID 21557715, compound

Participants

Reaction Steps

To a solution of 200 mg. of 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-5-carboethoxy-1,2,3-thiadiazole in 15 ml. of methanol is added a solution of 100 mg. of sodium hydroxide in 2 ml. of water, and the reaction mixture is refluxed for 4 hours. It is then cooled, evaporated to a small volume under vacuo, diluted with 25 ml. of water and extracted with ethyl acetate to eliminate the unsaponified product. The aqueous phase is passed through a column of 10 g. of ion exchange resin sold by the Dow Chemical Company under the trademark Dowex 50, acidic type (H+) eluting the column first with water and thereafter with 10% acetic acid solution. The combined acidic eluates are concentrated to a small volume under reduced pressure at low temperature and then lyophilized, to yield 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-5-carboxy-1,2,3-thiadiazole.

Provenance & Evidence