HCID 86632039, compound → HCID 23582778, compound

HRID 1092927Notes

Reaction equation

HRID 1092927 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]([C:36]([O:38]CC2C=CC=CC=2)=[O:37])=[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.O.[C].[Pd]>[NH2:11][CH:12]([CH2:23][CH2:24][P:25]([O:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([OH:38])=[O:37])=[CH:34][CH:35]=1)([O:27][CH3:28])=[O:26])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 2

HCID 86632039HCID 86632039, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23582778HCID 23582778, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Next, 1.40 g (2.22 mmol) of benzyl 2-(N-benzyloxycarbonylamino)-4-[4-(benzyloxycarbonyl)phenyl(methyl)phosphono]butanoate was dissolved in 28 mL of a solvent mixture of acetic acid and water at 2:1 and mixed with 200 mg of 5% palladium-carbon and hydrogen gas was introduced at room temperature for 2.2 hours. Thereafter, the palladium-carbon was removed by Celite filtration and the filtrate was vacuum-concentrated, and the residue was freeze-dried from water to obtain 2-amino-4-[4-carboxyphenyl(methyl)phosphono]butanoic acid (0.62 g, yield 89%) as a colorless solid.

Workup

  1. additionwas introduced at room temperature for 2.2 hours
  2. customThereafter, the palladium-carbon was removed by Celite filtration
  3. concentrationthe filtrate was vacuum-concentrated
  4. dry with materialthe residue was freeze-dried from water

Sources & evidence

ORD record
ord-7fa8d88dd3314a52a719f9201078236a
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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