Potassium Hydroxide → HCID 10093047, compound

Participants

Reaction Steps

4.2 g of l-menthyl (2S, 3S)-3-(2-amino-5-phenoxyphenyl)thio-2-hydroxy-3-(4- methoxyphenyl)propionate [prepared as described in step (a) above] were suspended in 42 ml of methanol, and a solution of 0.89 g of caustic potash dissolved in 5 ml of water was added to the resulting suspension. The resulting mixture was then stirred under reflux for 1 hour. At the end of this time, the methanol was removed by evaporation under reduced pressure, and 60 ml of Water and 60 ml of diethyl ether were added to the residue. The resulting mixture was stirred, and the ethereal layer was then removed. Ethyl acetate was added to the aqueous layer. after which 14.5 ml of 1N aqueous hydrochloric acid were added to neutralize the mixture. The ethyl acetate layer was then separated and dried over anhydrous anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure, and the residual gum Was crystallized using diethyl ether and diisopropyl ether. The crystals obtained were collected by filtration to afford 2.05 g of the title compound. melting at 151-152° C.

Provenance & Evidence