Sulfuric Acid → HCID 22808904, compound

Participants

Reaction Conditions

Reaction Steps

8.0 g (20 mmoles) of BOC--Nva--OH.DCHA are added to a mixture of 60 ml of ether and 20 ml of 2 n aqueous sulfuric acid, and the mixture is shaken until dissolution is complete. The etheral solution is separated, washed with 20 ml of 2 n aqueous sulfuric acid and water, dried, and evaporated in vacuo. The oily residue and 3.70 g (20 mmoles) of pentafluorophenol are dissolved in 25 ml of ethyl acetate, the solution is cooled to 0° C., 3.92 g (19 mmoles) of DCC are added, and the reaction is conducted for one hour. Thereafter the suspension is filtered, the filtrate is evaporated in vacuo, and the oily residue is dissolved in 50 ml of n-hexane. The solution is washed with 5×20 ml of 5% aqueous sodium bicarbonate solution and 2×20 ml of water and evaporated in vacuo. The oily residue solidified upon cooling. 6.21 g (81%) of BOC--Nva--OPFP are obtained; m.p.: 60°-62° C., Rf3 =0.70, [α]D :-32.3° C. (c=1.0, in dioxane).

Provenance & Evidence