Boron Trichloride → HCID 22405474, compound

Participants

Reaction Steps

To a solution of 2-[3-(5-methyl-1,3-dioxacyclohex-5-ylmethoxy-carbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.35 g) in methylene chloride (6 mL), cooled to 0° C. , was added dropwise 1.27 mL of a 10M methylene chloride solution of boron trichloride, and the reaction mixture allowed to warm to room temperature over 30 min. The reaction mixture was quenched by pouring into 25 mL of a 15% aqueous sodium chloride solution and stirring 15 min. Ethyl acetate (10 mL) was added, and the organic phase washed with brine, dried (MgSO4) and evaporated. Chromatography, using as eluant methylene chloride:methanol (20:1), followed by overnight vacuum-drying (50° C. at 27 Pa) yielded the title compound as a white solid (0.25 g); mp 94°-97° C. (dec); TLC: Rf =0.11, dichloromethane:methanol (95:5); 300 MHz NMR: 0.80 (s,3), 0.85 (s,3), 2.15 (m,1), 3.32 (2d,4), 3.98 (s,2), 4.4-4.6 (m,4), 4.65 (t,]), 6.25 (dd,1), 7.43 (m,5), 7.90 (d,1), 8.40 (d,1), 8.75 (d,1); IR(KBr): 3400 (broad), 2980, 1700, 1650, 1600, 1525, 1215 cm-1 ; MS: m/z=542(M+1).

Provenance & Evidence