HCID 86632035, compound → HCID 23582775, compound

HRID 1092923Notes

Reaction equation

HRID 1092923 reaction equation
C(OC([NH:11][CH:12]([CH2:23][CH2:24][P:25]([O:34][CH:35]([C:38](=[O:51])[NH:39][CH2:40][C:41]([O:43]CC1C=CC=CC=1)=[O:42])[CH2:36][CH3:37])([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][CH:35]([C:38](=[O:51])[NH:39][CH2:40][C:41]([OH:43])=[O:42])[CH2:36][CH3:37])([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 86632035HCID 86632035, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23582775HCID 23582775, compoundYield 177.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Next, 0.25 g (0.35 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[1-[N-(benzyloxycarbonylmethyl)carbamoyl]propyl(phenyl)phosphono]butanoate was dissolved in 30 mL of a solvent mixture of methanol and water at 20:1 and mixed with 200 mg of 5% palladium-carbon and hydrogen gas was introduced for 45 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-[1-[N-(carboxymethyl)carbamoyl]propyl(phenyl)phosphono]butanoic acid (250 mg, yield 18%) as a colorless solid.

Workup

  1. additionwas introduced for 45 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-38ac4ade79f14f9a8b1c147df8d328fc
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

Loading…