Acetic Acid → HCID 11071062, compound

Participants

Reaction Steps

After briskly stirring a mixture of N-(3,4-dimethyl-5-isoxazolyl)-2'-formyl-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide (100 mg; 0.24 mmol; prepared as in Step (F) of Example 21), isobutylmethylamine (0.087 ml; 0.71 mmol), AcOH (0.08 ml; 1.34 mmol) and 3 Å molecular sieves (670 mg) in 2 ml of CH2Cl2 for 1 hour at room temperature, sodium triacetoxyborohydride (150 mg; 0.71 mmol) was added. After stirring 18 hours at room temperature, the reaction mixture was filtered through celite and the filtrate was partitioned between EtOAc (40 ml) and saturated NaHCO3 solution (20 ml). The organic layer was washed with water (20 ml) followed by brine (20 ml). Drying (Na2 SO4) and concentration afforded a residue that was chromatographed on a 2.5×12 cm silica gel column using a stepwise gradient of 300 ml @CH2Cl2 to 5% MeOH/CH2Cl2 in 1% increments. The pure fractions were concentrated to afford 88 mg of the title compound of this Example as a white powder.

Provenance & Evidence