Water → HCID 23582779, compound

Participants

Reaction Steps

Next, 1.09 g (2.01 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[methyl(3-nitrophenyl)phosphono]butanoate and 1.30 g (12.0 mmol) of anisole were dissolved in 10 mL of dry nitromethane and mixed with 0.80 g (6.00 mmol) of aluminum trichloride and reaction was carried out at room temperature for 3 hours. Thereafter, 20 mL of water was added and stirred for 10 minutes. The mixture was washed with 50 mL of ether three times and the water layer was removed, and methanol was added to adjust the final concentration of methanol to be 30%. The solution was passed through a short column of neutral silica gel 60N to remove aluminum hydroxide. Without being concentrated, 30 mL of the effluent was purified by medium pressure reversed-phase column chromatography ODS-S-50B. The column was eluted with a linear gradient of 30 to 60% methanol at a flow rate of 6 mL/min and the fractions containing the compound eluted at 60% methanol were collected. The elution and purity of the compound were confirmed by TLC (BuOH/AcOH/H2O=5:2:2, ninhydrin coloration). After vacuum concentration, freeze drying was carried out from water to obtain 2-amino-4-[methyl(3-nitrophenyl)phosphono]butanoic acid (0.40 g, yield 63%) as a colorless solid.

Provenance & Evidence