4-Toluenesulfonyl chloride → HCID 131735585, compound

Participants

Reaction Steps

To a solution of {(S)-1-[(S)-1-(2-hydroxymethyl-2,3-dihydro-pyrrolo[2,3-b]pyridine-1-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (4.5 g, 10.36 mmol) in DCM (150 mL), was added triethylamine (4.25 mL, 31.106 mmol) followed by the slow addition of tosyl chloride (3.0 g, 15.55 mmol) at 0° C. The reaction mixture was stirred at rt for 16 hand then the reaction mixture was concentrated in vacuo. Water was added to the residue and the resulting mixture was extracted with EtOAc (300 mL×2). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, 18% EtOAc in hexanes) to give 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 (2.7 g) and toluene-4-sulfonic acid (R)-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 (1 g), m/z=589 (M+H).

Provenance & Evidence