Hydrochloric Acid → HCID 24989820, compound

Participants

Reaction Steps

A solution of 210 mg (0.94 mmol) (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one and 215 mg (0.94 mmol) (RS)-2-hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acid in 50 ml tetrahydrofuran were cooled to 0° C. and 129 mg (0.94 mmol) 1-hydroxy-benzotriazole hydrate, 327 μl (1.87 mmol) diisopropylethylamine and 183 mg (0.94 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride were added. Stirring was continued overnight at room temperature. The mixture was poured on ice/water and 1 N aqueous hydrochloric acid was added until pH=1 was reached. Extraction with first diethylether and second with ethylacetate, washing with saturated aqueous sodium hydrogen carbonate solution and brine and chromatography on silicagel with ethylacetate/heptane 2/1 yielded 150 mg (41%) (R/S)-2-hydroxy-2-methyl-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N′-(3,3,3-trifluoro-propyl)-malonamide as a white solid, MS (m/e): 436.1 (M+H)+.

Provenance & Evidence