Dicyclohexylcarbodiimide → HCID 59680788, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of D3 (33.72 g, 100 mmol) in DCM at 0° C., DMAP (3.66 g, 30 mmol), and E1 (34.33 g, 100 mmol) were added. After stirring 10 min at 0° C., DCC (22.7 g, 110 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight. Then the mixture was filtered and the filtrate concentrated to dryness. The residue was chased with ACN (100 ml), filtered again and the filtrate was concentrated. The residue was dissolved in EtOAc (200 ml) and partitioned successively between aq KHSO4 (100 ml, 10%), aq NaHCO3 (100 ml, sat.) and brine (100 ml). The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by flash LC (silica gel, grad EtOAc-Hex 1:4 to 1:2) to yield D2 (65.5 g, 98%). [α]D22−39.56 (c 1.06 CHCl3); Rf=0.55 (EtOAc:Hex 1:1).

Provenance & Evidence