1,1'-Carbonyldiimidazole → HCID 86604344, compound

Participants

Reaction Steps

A mixture of trans-2-methoxycinnamic acid (106 mg, 0.55 mmol) and carbonyldiimidazole (89 mg, 0.55 mmol) in THF (3 mL) was stirred at room temperature for 1 h, and then at 40° C. until gas evolution ceased. The mixture was cooled to room temperature and Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine (212 mg, 0.50 mmol) in solution in 1M K2CO3 was added. The reaction mixture was stirred at room temperature for 3 h, then diluted with 1N HCl and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo and purified by flash chromatography eluting with 70% EtOAc in hexane containing 0.4% AcOH to give the title compound (71% yield).

Provenance & Evidence