Phenol → HCID 69231925, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[4-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (0.44 mmol, 0.24 g), phenol (0.53 mmol, 0.050 g), K3PO4 (0.88 mmol, 0.19 g), 2-(di-t-butylphosphino)biphenyl (0.066 mmol, 0.020 g), and Pd(OAc)2 (0.044 mmol, 0.010 g) in toluene (7 mL) was degassed under vacuum and backfilled with nitrogen (3×) and heated at 110° C. for 18 h. Additional Pd(OAc)2 (10 mg) and 2-(di-t-butylphosphino)biphenyl (20 mg) were added to ensure complete reaction, and the mixture was heated 5 h. Upon cooling, the mixture was placed directly onto a silica gel column and eluted with 30%-50% EtOAc/hexanes to give 3-(2-(isopropoxycarbonylamino-methyl)-4-{2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid tert-butyl ester (0.11 g).

Provenance & Evidence