Dimethylformamide → HCID 178511794, compound

Participants

Reaction Steps

To a solution of HOBT (0.48 g, 3.5 mmol) in DMF (10 mL) was added Fmoc-D-His(Tr)-CO2H (2.0 g, 3.2 mmol) followed by EDAC (0.67 g, 3.5 mmol). The mixture was stirred at room temperature for 20 minutes before adding a solution of Tyr(OBn)-CONH(CH2)3OPh (from Step 2 above, 1.4 g, 3.2 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature before partitioning between a mixture of water (20 mL) and 1:1 Et2O:EtOAc (50 mL). The layers were separated, and the organic phase was washed with saturated aqueous NaCl (4×20 mL) and dried (MgSO4). Filtration and concentration in vacuo provided an oil which was further purified by flash chromatography (SiO2, CHCl3 : MeOH eluent) to give the protected His-Tyr dipeptide; FAB-MS 1006 (m).

Provenance & Evidence