Example 134 (±)-5-[Acetyl-(3,5-bis(trifluoromethyl)benzyl)amino]-6-fluoro-tetrahydrobenzo[b]azepine-1-carboxylic acid Synthesis Procedure 1. Methyl 2-amino-6-fluorobenzoate Preparation: 2-amino-6-fluorobenzoic acid (3.00 g, 19.3 mmol) was dissolved in a ethyl acetate (59 mL) and ethanol (59 mL) (59 mL) and ethanol (59 mL) in a mixed solvent. Trimethylsilylated diazomethane (19.3 mL, 38.68 mmol, 2M in hexane) was slowly added to this solution and the reaction mixture was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to afford methyl 2-amino-6-fluorobenzoate (3.26 g, quantitative yield). Mass spectrum (electrospray positive ion mode): m/z 170 [M+H]+.
