Hydrochloric Acid → 2-{3-(4-Chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N-{2-formamido-2-[3-(trifluoromethyl)phenyl]propyl}acetamide

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Reaction Steps

At RT, 12 μl (68 μmol) of N,N-diisopropylethylamine and then 11 mg (65 μmol) of 4-nitrophenyl formate were added to a solution of 38 mg (62 μmol) of the compound of Example 53A in 1 ml of THF, and the mixture was stirred at RT. After 1 h, another 10 mg (62 μmol) of 4-nitrophenyl formate were added and stirring of the reaction mixture was continued overnight. Since LC/MS analysis indicated additional formation of an O-formylated byproduct, 248 μl of a 1 N solution of lithium hydroxide in water were added to the reaction mixture. After 1 h, the mixture was acidified with 1 N hydrochloric acid and separated by preparative HPLC [Method 8]. This gave 30 mg (81% of theory) of the title compound as a diastereomer mixture.

Provenance & Evidence