Hydrochloric Acid → (-)-cis-Isocitric acid lactone

Participants

Reaction Conditions

Reaction Steps

16.49 g of 3-tert-butyl 1,2-diethyl (1S,2R)-1-hydroxy-1,2,3-propanetricarboxylate, 100 ml of acetic acid and 50 ml of concentrated hydrochloric acid were mixed and stirred at 70° C. for 5 hours. The acetic acid and hydrochloric acid were evaporated in vacuo, and the residue was dissolved in 100 ml of acetic acid and 50 ml of concentrated hydrochloric acid again. The resulting solution was stirred at 70° C. for 12 hours. The acetic acid and hydrochloric acid were evaporated in vacuo, and the residue was stirred in 100 ml of trifluoroacetic acid at 60° C. for 5 hours. The trifluoroacetic acid was evaporated in vacuo, and the residue was crystallized in hexane-ethyl acetate to give 9.38 g of the title compound as a white powder.

Provenance & Evidence