Reaktion #1180099

Reaktionsgleichung

water

benzyl 2-(N-benzyloxycarbonylamino)-4-[(4-chlorophenyl)(methyl)phosphono]butanoate

anisole

aluminum trichloride

→

2-amino-4-[(4-chlorophenyl)(methyl)phosphono]butanoic acid

Ausbeute 57.0%

Lösungsmittel

nitromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle