Dicyclohexylcarbodiimide → Fmoc-NH-L-Ile-D-Phe-CH2OH

Participants

Reaction Conditions

Reaction Steps

(R)(+)-2-amino-3-phenyl-1-propanol (427 mg, 2.83 mmol) dissolved in dry DMF (20 mL), stirred under nitrogen, to this stirred mixture at 25° C. DCC (699 mg, 3.39 mmol), HOBt (457 mg, 3.38 mmol) was added with constant stirring. After 10 minutes of stirring N-(9-fluorenylmethoxycarbonyl)-L-isoleucine (1.0 g, 2.83 mmol) was added to the above mixture and then stirred at 25° C. for 14 h. After 14 h white colored crystals precipitated out (DCU), which was filtered. The filterate was checked on TLC (2% MeOH: CH2Cl2) which showed formation of a new compound at higher Rf (0.6), LC/MS also showed molecular ion peak corresponding to the dipeptide 1a with other impurities peaks. The crude product was chromatographed on silica gel (Silica gel 60, 63-200μ) column and eluted with 2% MeOH: CH2Cl2 to give 650 mg of the dipeptide Fmoc-NH-L-Ile-D-Phe-CH2OH (1a) as a white solid. Checked on LC/MS which showed M++1 (487.4) and M++Na (509.2).

Provenance & Evidence