HCID 86632034, compound → HCID 23582774, compound

HRID 1092921Notes

Reaction equation

HRID 1092921 reaction equation
C(OC([NH:11][CH:12]([CH2:23][CH2:24][P:25]([O:34][CH2:35][CH2:36][CH2:37][CH3:38])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[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:34][CH2:35][CH2:36][CH2:37][CH3:38])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 2

HCID 86632034HCID 86632034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23582774HCID 23582774, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Next, 0.64 g (1.19 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[butyl(phenyl)phosphono]butanoate was dissolved in 20 mL of a solvent mixture of methanol and water at 3:1 and mixed with 200 mg of 5% palladium-carbon and hydrogen gas was introduced for 75 minutes. The palladium-carbon was removed by Celite filtration and the filtrate was vacuum-concentrated. The residue 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 60% 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-[butyl(phenyl)phosphono]butanoic acid (0.28 g, yield 75%) as a colorless solid.

Workup

  1. additionwas introduced for 75 minutes
  2. customThe palladium-carbon was removed by Celite filtration
  3. concentrationthe filtrate was vacuum-concentrated
  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 30 to 60% methanol at a flow rate of 6 mL/min
  6. additionthe fractions containing the compound
  7. washeluted at 60% methanol
  8. customwere collected
  9. washThe elution and purity of the compound
  10. concentrationAfter vacuum concentration, freeze
  11. customdrying

Sources & evidence

ORD record
ord-4e744b9e259d484f8050f2d511f33a66
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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