Water → HCID 86632032, compound

HRID 1092919Notes

Reaction equation

HRID 1092919 reaction equation
C(OC([NH:11][CH:12]([CH2:23][CH2:24][P:25]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1)([O:27][CH3:28])=[O:26])[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=O)C1C=CC=CC=1.C1(OC)C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3].O>[N+](C)([O-])=O>[NH2:11][CH:12]([CH2:23][CH2:24][P:25]([O:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]#[N:37])=[CH:34][CH:35]=1)([O:27][CH3:28])=[O:26])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 86632033HCID 86632033, compound

Product 1

HCID 86632032HCID 86632032, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Next, 0.95 g (1.82 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[(4-cyanophenyl)(methyl)phosphono]butanoate and 1.18 g (10.9 mmol) of anisole were dissolved in 10 mL of dry nitromethane and mixed with 0.73 g (5.46 mmol) of aluminum trichloride at room temperature. 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 an ether three times and a 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 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 45% 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 to obtain 2-amino-4-[(4-cyanophenyl)(methyl)phosphono]butanoic acid (0.38 g, yield 70%) as a colorless solid.

Workup

  1. stirringstirred for 10 minutes
  2. washThe mixture was washed with 50 mL of an ether three times
  3. customa water layer was separated
  4. additionmethanol was added
  5. customto remove aluminum hydroxide
  6. concentrationWithout being concentrated
  7. customthe effluent was purified by medium pressure reversed-phase column chromatography ODS-S-50B
  8. washThe column was eluted with a linear gradient of 30 to 60% methanol at a flow rate of 6 mL/min
  9. additionthe fractions containing the compound
  10. washeluted at 45% methanol
  11. customwere collected
  12. washThe elution and purity of the compound
  13. concentrationAfter vacuum concentration, freeze
  14. customdrying

Sources & evidence

ORD record
ord-79489d7975f84589a0c8e433de031696
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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