4-Nitrophenol → 10-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid p-nitrophenyl ester

Participants

Reaction Steps

10-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid (236.9 mg, 0.7 mmol) and p-nitrophenol (107.1 mg, 0.77 mmol) were dissolved in acetonitrile (2 ml). To this solution was added DCC (158.9 mg, 0.77 mmol) under ice-cooling. The solution was stirred at room temperature for 16 hours. The insoluble material was removed by filtration and the solvent was evaporated under reduced pressure. The residue was chromatographed on a silica gel column with chloroform as eluent to obtain about 5 m mol of 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid p-nitrophenyl ester. The ester was dissolved in DMF (1.5 ml). To this solution was added methyl 1-α-O-benzyl-N-acetylmuramyl-L-valyl-D-isoglutaminate (0.15 g, 0.25 mmol), HoBt(0.14 g, 1 mmol) and NEM (128 μl, 1 mmol) and the reaction mixture was stirred at room temperature for four days. After evaporation, the residue was purified by the chromatography on a silica gel column with chloroform/acetone/methanol (10:3:1, v/v) as eluent and precipitated as a gel from ethanol/ether to obtain methyl 1-α-O-benzyl-6-O-{10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoyl}-N-acetylmuramyl-L-valyl-D-isoglutaminate (0.13 g). [α]D22 +71.8° (C 0.5, DMF). Rf4 =0.70.

Provenance & Evidence