Sodium Azide → HCID 117871264, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of toluene-4-sulfonic acid (S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-3-methyl-butyryl}-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-2-ylmethyl ester (Intermediate 2) (200 mg, 0.34 mmol) in DMF (4 mL) was added NaN3 (26.53 mg, 0.408 mmol) and the resulting mixture was heated at 90° C. for 3 h. The reaction was concentrated in vacuo and the obtained residue was dissolved in ethyl acetate (25 mL) and washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, 12% EtOAc in hexanes) to give {(S)-1-[(S)-1-((S)-2-azidomethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (140 mg), m/z=460 (M+H).

Provenance & Evidence