N-tert-Butoxycarbonyl-L-tryptophan → (3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one

Participants

Reaction Steps

To a solution of N-tert-butoxycarbonyl-L-tryptophan (0.70 g) in acetonitrile (20 ml) was added dropwise a solution of (3RS)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (1.00 g) in methylene chloride (5 ml) under stirring at ambient temperature. The mixture was stirred overnight. The precipitate was collected by filtration and the colorless solid was partitioned between methylene chloride and 0.5N NaOH. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford (3S)-3-amino-1-{(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl}-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (0.46 g) as s colorless crystal.

Provenance & Evidence