Chlorosuccinimide → HCID 24765971, compound

Participants

Reaction Conditions

Reaction Steps

Into a solution of Compound 67 (206 mg, 0.50 mmol) in 2-propanol (1.0 mL) was added hydroxylamine hydrochloride (35 mg, 0.50 mmol). Water was added (4 drops). The mixture was heated to 80° C. for 1 hour, cooled to room temperature, concentrated under reduced pressure. The residue was taken up in ethyl acetate (4.0 mL). The mixture was cooled to 0° C. Into the mixture, water (4 drops), NaHCO3 (84 mg, 1.0 mmol), trimethylsilyl acetylene (0.50 mL, 3.60 mmol), and N-chlorosuccinimide (134 mg, 1.00 mmol) were added sequentially. The mixture was stirred at room temperature overnight, diluted with ethyl acetate, washed with water then with brine, and dried (Na2SO4), filtered and concentrated. The residue was purified on silica to give Compound 105 (110 mg).

Provenance & Evidence