Propionic Acid → HCID 59094512, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3aR,4R,6R,6aR)-N′-hydroxy-6-methoxy-2,2-dimethyl tetrahydrofuro[3,4-d][1,3]dioxole-4-carboximidamide (Preparation 35) (1.1 g, 4.74 mmol), propionic acid (0.39 g, 5.27 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.1 g, 5.74 mmol) in diethylene glycol dimethyl ether (10 ml) was heated under reflux at 60° C. for twelve hours and then heated at 110° C. for a further 3 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between water (50 ml) and a mixture of ether (25 ml) and pentane (25 ml). The organic phase was separated and the aqueous layer was extracted with more ether/pentane mixture (50 ml). The combined organic extracts were dried (anhydrous magnesium sulphate) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of diethyl ether:pentane (1:2 by volume) gradually changing to diethyl ether:pentane (1:1 by volume) to give the title compound (0.87 g).

Provenance & Evidence