Diisopropylethylamine → (r/s)-2-Hydroxy-2-methyl-n-[(s)-6-oxo-5-(2,2,2-trifluoro-ethyl)-6,7-dihydro-5h-dibenzo[b,d]azepin-7-yl]-n-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Participants

Reaction Steps

A solution of 144 mg (0.47 mmol) (S)-7-amino-5-(2,2,2-trifluoro-ethyl)-5H,7H-dibenzo[b,d]azepin-6-one and 125 mg (0.47 mmol) (RS)-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid in 21 ml tetrahydrofuran were reacted at room temperature with 73.6 mg (0.47 mmol) 1-hydroxy-benzotriazole hydrate, 165 μl (0.94 mmol) diisopropylethylamine and 92.1 mg (0.47 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride. Stirring was continued overnight. Removal of the solvent by distillation and chromatography on silicagel with ethylacetate/heptane (gradient 15/85 to 40/60) yielded 207 mg (79%) (R/S)-2-hydroxy-2-methyl-N-[(S)-6-oxo-5-(2,2,2-trifluoro-ethyl)-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide as a white solid, MS (m/e): 554.3 (M+H)+.

Provenance & Evidence