HCID 131729487, compound → HCID 86260200, compound

HRID 1092916Notes

Reaction equation

HRID 1092916 reaction equation
[N+](C1C=CC(COC([NH:12][CH:13]([CH2:24][CH2:25][P:26]([O:35][CH3:36])([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:27])[C:14]([O:16]CC2C=CC=CC=2)=[O:15])=O)=CC=1)([O-])=O.[H][H]>C(O)(=O)C.[C].[Pd]>[NH2:12][CH:13]([CH2:24][CH2:25][P:26]([O:35][CH3:36])([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 131729487HCID 131729487, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86260200HCID 86260200, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Next, 0.57 g (1.05 mmol) of benzyl 2-(N-4-nitrobenzyloxycarbonylamino)-4-[methyl(phenyl)phosphono]butanoate was dissolved in 20 mL of acetic acid and mixed with 210 mg of 10% palladium-carbon and hydrogen gas was introduced for 2 hours. The palladium-carbon was removed by Celite filtration and the filtrate was concentrated in reduced pressure. The residue was purified by medium pressure reversed-phase column chromatography ODS-S-50B. The column was eluted with a linear gradient of 4 to 50% acetonitrile (12 mL/min flow rate) and the fractions of the compound eluted with 5% acetonitrile were collected and 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-[methyl(phenyl)phosphono]butanoic acid (0.14 g, yield 48%) as a colorless solid.

Workup

  1. additionwas introduced for 2 hours
  2. customThe palladium-carbon was removed by Celite filtration
  3. concentrationthe filtrate was concentrated in reduced pressure
  4. customThe residue was purified by medium pressure reversed-phase column chromatography ODS-S-50B
  5. washThe column was eluted with a linear gradient of 4 to 50% acetonitrile (12 mL/min flow rate)
  6. washthe fractions of the compound eluted with 5% acetonitrile
  7. customwere collected
  8. washthe elution and purity of the compound
  9. concentrationAfter vacuum concentration, freeze
  10. customdrying

Sources & evidence

ORD record
ord-8f35180874804a07a6739384b8b72b28
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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