N,N-Dimethylglycine → HCID 67351665, compound

Participants

Reaction Steps

To a solution of (S)-2-tert-Butoxycarbonylamino-3-[4-hydroxy-phenyl]-propionic acid methyl ester (2 g, 6.8 mmol, 1 eq.) in dioxane (20 ml) was added 4-bromochlorobenzene (1.95 g, 10 mmol, 1.5 eq.), CuI(I) (140 mg, 0.7 mmol, 0.1 eq.), N,N-dimethylglycine (220 mg, 2.1 mmol, 0.3 eq.) and cesium carbonate (4.6 g, 14 mmol, 3 eq.). The resulting mixture was stirred under Ar at reflux overnight. After cooling to room temperature, the volatile material was removed under reduced pressure to give a residue, which was partitioned between water and ethyl acetate. The ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined ethyl acetate layers were dried over anhydrous MgSO4. Evaporation of solvent under reduced pressure gave a residue, which was purified by chromatography on silica gel using dichloromethane/MeOH (50:1) as eluent to give the desired product (587 mg, 21% yield).

Provenance & Evidence