Boron Trichloride → HCID 178429230, compound

Participants

Reaction Conditions

Reaction Steps

The product from Example 94 (95 mg, 0.19 mmol, 1.0 equiv) was cooled to −78° C. in 2.0 mL CH2Cl2 and BCl3 (1.0 M in CH2Cl2, 2.90 mL, 2.91 mmol, 15.0 equiv) was added dropwise. The reaction was warmed to 35° C. and stirred for 90 hours. An additional portion of BCl3 (2.90 mL, 2.91 mmol, 15.0 equiv) was added dropwise and the reaction was stirred for another 96 hours. The reaction mixture was diluted with EtOAc and water and basified to pH 14 with 6N NaOH. The phases were separated, and the aqueous phase was acidified to pH 4 with 6N HCl. The precipitate was filtered and washed with Et2O. The residue was purified by reverse-phase HPLC (10-95% CH3CN/H2O, 0.1% TFA over 18 minutes, retention time 10.63 min) to provide 25 mg (27%) of the title compound as a white solid. MS (ES+) m/e 476 [M+H]+

Provenance & Evidence