Pyridine → Trifluoroacetic acid

Participants

Reaction Steps

Analogously to example 23 the solution of 1.7 gm of (2-{2-[2-(2-Carbamoyl-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(5-hydroxy-adamantan-2-yl)-2-oxo-ethylcarbamoyl]-pyrrolidin-1-yl}-1-methyl-2-oxo-ethyl)-carbamic acid tert-butyl ester in THF was added into the mixture of pyridine (1.0 ml) and Trifluoro acetic anhydride (0.95 ml). The reaction mixture was stirred at room temperature. THF was evaporated and residue was taken into MeOH and 10 ml 10% K2CO3 solution was added. MeOH was evaporated and aq. layer was extracted with EtoAC. The combined EtoAC layers were washed with 1N HCl and aq. NaHCO3, dried over sodium sulphate and concentrated in vacuum to give crude product. The crude product was purified by column chromatography to get pure Trifluoro acetic acid salt of 1-(2-Amino-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid [2-(2-cyano-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(5-hydroxy-adamantan-2-yl)-2-oxo-ethyl]-amide of formula 37. (Yield: 0.7 gm)

Provenance & Evidence