Oxalyl chloride → HCID 58288339, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C., 155 μl (0.31 mmol) of a 2 M solution of oxalyl chloride in dichloromethane and one drop of DMF were added to a solution of 41.3 mg (0.16 mmol) of (2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoic acid in 1.16 ml of dichloromethane. After 1 h of stirring at 0° C., the mixture was concentrated, the residue that remained was dissolved in 1 ml of THF, 32 μl (0.19 mmol) of N,N-diisopropylethylamine were added, the mixture was cooled to 0° C. and a solution of 42 mg (0.17 mmol) of tert-butyl 3-(3-amino-4-cyanophenyl)propanoate in 2 ml of THF was added. The reaction mixture was stirred at RT overnight. The mixture was then poured into 10 ml of water and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by preparative HPLC. This gave 16.5 mg (22% of theory) of the title compound.

Provenance & Evidence