Sodium Hydroxide → (R)-5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-methyl 5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoate (300 mg, 1.13 mmol) in methanol (2.0 mL) and dichloromethane (1.0 mL) was added 2.0M aqueous sodium hydroxide solution (2.0 mL, 4.0 mmol). The reaction mixture was heated to 45° C. and stirred for 2 h, at which time it was cooled to room temperature and all volatiles were removed by rotary evaporation. To the residual solution was slowly added 1.0M aqueous hydrochloric acid until pH<2. The yellow precipitate was collected by filtration and washed with water to afford (R)-5-(sec-butylamino)-4-(aminocarbonyl)-2-methylbenzoic acid (210 mg, 65%). MS (EI) for C13H18N2O3: 251 (MH+).

Provenance & Evidence