DL-valine → HCID 18696372, compound

Participants

Reaction Steps

To a suspension of bicyclo[2.2.2]oct-5-en-2,3-dicarboxylic anhydride (2.01 g, 11.3 mmol) in H2O (25 mL) was added (dl)-valine (1.58 g, 13.5 mmol) and a solution of K2CO3 (934 mg, 6.8 mmol) in H2O (3 mL). The mixture was heated to reflux temperature and allowed to react for 4 hrs. After cooling to room temperature, the mixture was washed with EtOAc, acidified with conc. HCl until the pH reached 1 and extracted with EtOAc. The organic layer was washed with 5% HCl followed by brine and then dried over Na2SO4. Removal of the solvent gave a beige solid which was recrystallized from EtOAc/hexane to yield the product as off-white crystals: 1.72 g (55% yield), mp=156° C.

Provenance & Evidence