Potassium Bicarbonate → HCID 178490238, compound

Participants

Reaction Steps

1 ml of a 3/2 dichloromethane/trifluoroacetic acid solution is added to 84 mg (0.193 mmol) of (S)-2-[(S)-2-benzoylamino-3-(1H-imidazol-4-yl)propionylamino]-3-(4-methoxyphenyl)propanoic acid (cf. procedure 1-1). After stirring at ambient temperature for 1 hour, the solvents are evaporated off. The residue obtained is dissolved in 1 ml of DMF, and 79 mg (0.246 mmol) of TBTU and 15 drops of DIEA are added. 0.235 mmol of 3-cyclohexylazetidin-3-ol trifluoroacetate dissolved in 1 ml of a DCM solution is added dropwise and stirred at ambient temperature for 2 hours. A saturated solution of potassium hydrogen carbonate is added, followed by extraction with dichloromethane. The organic phase is washed with a saturated solution of potassium hydrogen carbonate. The organic phase is dried and evaporated to dryness. The crude product obtained is purified by silica gel chromatography (eluent 85/15 dichloro-methane/methanol mixture). 35 mg of N—[(S)-1-[(S)-2-(3-cyclohexyl-3-hydroxyazetidin-1-yl)-1-(4-methoxybenzyl)-2-oxoethylcarbamoyl]-2-(1H-imidazol-4-yl)ethyl]benzamide are obtained in the form of a yellow powder with a yield of 32%.

Provenance & Evidence