HCID 86632027, compound → HCID 57751973, compound

HRID 1092915Notes

Reaction equation

HRID 1092915 reaction equation
C(OC([NH:11][CH:12]([CH2:23][CH2:24][P:25]([O:35][CH3:36])([O:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)=[O:26])[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=O)C1C=CC=CC=1.[H][H]>CO.O.[C].[Pd]>[NH2:11][CH:12]([CH2:23][CH2:24][P:25]([O:35][CH3:36])([O:27][C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)=[O:26])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 2

HCID 86632027HCID 86632027, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57751973HCID 57751973, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Next, 0.70 g (1.37 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[methyl(4-methylphenyl)phosphono]butanoate was dissolved in 30 mL of a solvent mixture of methanol and water at 2:1 and mixed with 270 mg of 5% palladium-carbon and hydrogen gas was introduced for 2 hours. The palladium-carbon was removed by Celite filtration and the filtrate was concentrated under a reduced pressure. The residue was purified by medium pressure reversed-phase column chromatography ODS-S-50B (Yamazen Co., Ltd., Osaka). The column was eluted with a linear gradient of 30 to 60% methanol (6 mL/min flow rate) and the fractions of the compound eluted with 60% methanol were collected. After the elution and purity of the compound were confirmed by TLC (BuOH/AcOH/H2O=5:2:2, ninhydrin coloration), vacuum concentration and freeze drying were carried out to obtain 2-amino-4-[methyl(4-methylphenyl)phosphono]butanoic acid (0.20 g, yield 51%) 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 under a reduced pressure
  4. customThe residue was purified by medium pressure reversed-phase column chromatography
  5. washThe column was eluted with a linear gradient of 30 to 60% methanol (6 mL/min flow rate)
  6. washthe fractions of the compound eluted with 60% methanol
  7. customwere collected
  8. washAfter the elution and purity of the compound
  9. concentrationwere confirmed by TLC (BuOH/AcOH/H2O=5:2:2, ninhydrin coloration), vacuum concentration and freeze
  10. customdrying

Sources & evidence

ORD record
ord-da8348c265004528850d2d22146bb1ac
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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