反应详情

Next, 0.73 g (1.37 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[(4-chlorophenyl)(methyl)phosphono]butanoate and 0.89 g (8.22 mmol) of anisole were dissolved in 10 mL of dry nitromethane and mixed with 0.55 g (4.11 mmol) of aluminum trichloride. After stirring was carried out at room temperature for 1 hour, 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 separated 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, the eluent was purified by medium pressure reversed-phase column chromatography ODS-S-50B. The column was eluted with 40% methanol at a flow rate of 6 mL/min and the fractions of the compound 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 to obtain 2-amino-4-[(4-chlorophenyl)(methyl)phosphono]butanoic acid (0.24 g, yield 57%) as a colorless solid.

1. stirringstirred for 10 minutes
2. washThe mixture was washed with 50 mL of ether three times
3. customthe water layer was separated
4. additionmethanol was added
5. customto remove aluminum hydroxide
6. concentrationWithout being concentrated
7. customthe eluent was purified by medium pressure reversed-phase column chromatography ODS-S-50B
8. washThe column was eluted with 40% methanol at a flow rate of 6 mL/min
9. customthe fractions of the compound were collected
10. washThe elution and purity of the compound
11. concentrationAfter vacuum concentration, freeze
12. customdrying