Triethylamine → (4-Oxo-1,2,3-benzotriazin-3-yl) 4-[4-(4-chlorophenyl)-9-oxo-11-sulfanylidene-5-oxa-1,10-diazatricyclo[6.3.0.02,6]undeca-2(6),3,7-trien-10-yl]-3,3-dimethylbutanoate

Participants

Reaction Conditions

Reaction Steps

Compound 11 (105 mg, 0.25 mmol) was dissolved in dry THF (5 ml) and 3-hydroxy-dihydrobenzotriazinone (HODhbt; 49 mg, 0.3 mmol, 1.2 molequivalents) was added thereto, followed by addition of Et3N (51 mg, 0.5 mmol, 2 molequivalents) and 4-dimethylaminopyridine (DMAP; 15 mg, 0.125 mmol, 0.5 molequivalents). The reaction mixture was stirred at 25° C. for 16 hours while being monitored by TLC using a 6:4 hexane:EtOAc mixture as an eluent, until the appearance of a less polar spot, attributed to the active ester intermediate, was observed. Chloroform was thereafter added and the resulting mixture was washed with 1 M HCl, dried (Na2SO4) and the solvents were removed under reduced pressure to give a red solid. Chromatography was carried out using a 9:1 hexane:ethyl acetate mixture as eluent to give Compound 12 (38 mg, 20% yield) as a orange solid.

Provenance & Evidence