HCID 131723243, compound → HCID 58726315, compound

Participants

Reaction Steps

The dipeptide compound Z-Phe-D-Pro-OtBu (700 mg, 1.45 mmol) obtained in step 1-1 was dissolved in acetic acid (5 ml) and stirred overnight (about 14 hours) under hydrogen atmosphere in the presence of 5% Pd/C (70 mg). After the reaction mixture was filtered and concentrated, an oily residue was dissolved in ethyl acetate and washed with 4% NaHCO3. After being dried over anhydrous sodium carbonate, the product was concentrated to yield H-Phe-D-Pro-OtBu (425 mg, 92%). The concentrate was redissolved in DMF (5 ml), and Z-Phe-OH (434 mg, 1.45 mmol) and HOBt. H2O (245 mg, 1.60 mmol) were added, followed by adding DCC (230 mg, 1.60 mmol) under ice cooling, and as such the mixture was stirred overnight. The reaction mixture was filtered, concentrated, redissolved in ethyl acetate, and washed sequentially with 10% citric acid, 4% NaHCO3 and with saturated aqueous sodium chloride solution. After being dried over MgSO4 and concentrated, the residue was purified by flash silica gel chromatography (CHCl3) to yield 720 mg (90%) of the titled tripeptide compound as a foamy material.

Provenance & Evidence