Dimethylformamide → HCID 178511794, compound

Participants

Reaction Steps

To a solution of HOBT (2.6 g, 19.3 mmol) in DMF (10 mL) was added Fmoc-His(Tr) (10.0 g, 16.1 mmol) followed by EDAC (3.7 g, 19.3 mmol). The mixture was stirred at room temperature for 20 minutes before adding a solution of Tyr(OBn)-CO2CH2CH2TMS (from Step 2 above, 5.8 g, 16.1 mmol) in DMF (10 mL). The mixture was stirred overnight at room temperature before partitioning between a mixture of water 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 974 (m+1).

Provenance & Evidence