HCID 86632038, compound → HCID 23582777, compound

HRID 1092926Notes

Reaction equation

HRID 1092926 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]([CH2:36][C:37]([O:39]CC2C=CC=CC=2)=[O:38])=[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.[H][H]>C(O)(=O)C.[C].[Pd]>[NH2:11][CH:12]([CH2:23][CH2:24][P:25]([O:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][C:37]([OH:39])=[O:38])=[CH:34][CH:35]=1)([O:27][CH3:28])=[O:26])[C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 86632038HCID 86632038, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23582777HCID 23582777, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Next, 1.25 g (1.94 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-{[4-(benzyloxycarbonylmethyl)phenyl] (methyl)phosphono}butanoate was dissolved in 20 mL of acetic acid and mixed with 200 mg of 5% palladium-carbon and hydrogen gas was introduced at room temperature for 3.5 hours. Thereafter, the palladium-carbon was removed by Celite filtration and the filtrate was vacuum-concentrated and the residue was purified by medium pressure reversed-phase 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 of the compound eluted with 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 from water were carried out to obtain 2-amino-4-{[4-(carboxymethyl)phenyl](methyl)phosphono}butanoic acid (0.41 g, yield 64%) as a colorless solid.

Workup

  1. additionwas introduced at room temperature for 3.5 hours
  2. customThereafter, the palladium-carbon was removed by Celite filtration
  3. concentrationthe filtrate was vacuum-concentrated
  4. customthe residue was purified by medium pressure reversed-phase 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. washthe fractions of the compound eluted with 60% methanol
  7. customwere collected
  8. washThe elution and purity of the compound
  9. concentrationAfter vacuum concentration, freeze
  10. dry with materialdrying from water

Sources & evidence

ORD record
ord-0a2eee9131a14973845739c5bf9c3fe6
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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