Sodium Hydroxide → HCID 60083753, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxycarbonyl-5-(2-chloro-6-fluorophenyl)oxazole (236 mg, 0.927 mmol), MeOH (5 ml), THF (1 ml), and 2N NaOH (1.5 ml, 3.00 mmol) was heated to 50° C. for 30 minutes. The mixture was cooled to room temperature and H2O and ice were added followed by acidification to pH 2 and extraction with EtOAc. The organic fraction was washed (brine), dried (Na2SO4), filtered, and concentrated to give the crude carboxylic acid. The crude carboxylic acid, 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide (292 mg, 0.927 mmol), EDCI (354 mg, 1.85 mmol), and DMAP (11 mg, 0.093 mmol) were allowed to react in CH2Cl2 (5 ml) for 15 h at room temperature under N2. The mixture was applied directly to a silica gel column and elution with hexanes/EtOAc (gradient) gave the title compound (193 mg, 39%).

Provenance & Evidence