Hydrochloric Acid → HCID 86654808, compound

Participants

Reaction Steps

A solution of the product from EXAMPLE 3 (4, 32 mg, 64 μMol) in THF (6 mL) was treated with 1N HCl (0.6 mL) was kept at 45-47° C. for 24 hours. The reaction mixture was cooled to room temperature. TLC (DCM-MeOH 95:5) shows no 4 (Rf=0.75) and one major product (Rf=0.4). The solution was concentrated on a rotary evaporator to remove THF. The resulting mixture was partitioned between EtOAc (25 mL) and saturated aqueous NaCl (25 mL). The organic layer was separated and allowed to stand for 15 minutes. The organic solution was decanted from some aqueous droplets. It was then evaporated at reduced pressure to give an orange solid. The solid was dissolved in 0.25 M LiOH (1 mL, 0.25 mMol). The resulting black solution was stirred at room temperature for 24 hours. The reaction mixture was then acidified by dropwise addition of concentrated HCl (3 drops from a Pasteur pipet) to give a slurry of an orange solid. The slurry was cooled on an ice bath for 10 minutes then the solid was collected by filtration, rinsing with ice-cold water (2×2 mL) and Et2O (2×2 mL). The solid was then dried under vacuum for 6 hours to afford 5 (13.5 mg, 51%). MS (AP− taken from a MeOH solution) 444 (M+MeOH−1), 412 (m−1). NMR (DMSO-d6, δ), 13.55 (br, 1H, CO2H), 12.65 (br, 1H, CO2H), 12.02 (br, 1H, CONH), 11.83 (br, 1H, NH), 8.24 (s, 1H, H-8), 7.20 (s, 1H, H-3), 5.87 (m, 1H, vinyl-H), 5.05 (dd, 1H, vinyl-H), 4.99 (dd, 1H, vinyl-H), 4.03 (t, 2H, OCH2), 2.18 (q, 2H, allyl-CH2), 1.75 (m, 2H, CH2).

Provenance & Evidence