HCID 87063274, compound → HCID 23582839, compound

HRID 1092930Notes

Reaction equation

HRID 1092930 reaction equation
[N+](C1C=CC(COC([NH:12][CH:13]([CH2:24][CH2:25][P:26]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:27])[C:14]([O:16]CC2C=CC=CC=2)=[O:15])=O)=CC=1)([O-])=O.[H][H]>C(O)(=O)C.[C].[Pd]>[NH2:12][CH:13]([CH2:24][CH2:25][P:26]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 87063274HCID 87063274, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23582839HCID 23582839, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Next, 0.64 g (1.06 mmol) of benzyl 2-(N-4-nitrobenzyloxycarbonylamino)-4-(diphenylphosphono)butanoate was dissolved in 20 mL of acetic acid and mixed with 86 mg of 10% palladium-carbon and hydrogen gas was introduced at room temperature for 2 hours. Thereafter, the palladium-carbon was removed by Celite filtration and the filtrate was vacuum-concentrated, and the residue was crystallized from a solvent mixture of acetonitrile and water to obtain 2-amino-4-(diphenylphosphono)butanoic acid (0.13 g, yield 37%) as a colorless solid.

Workup

  1. additionwas introduced at room temperature for 2 hours
  2. customThereafter, the palladium-carbon was removed by Celite filtration
  3. concentrationthe filtrate was vacuum-concentrated
  4. customthe residue was crystallized from a solvent mixture of acetonitrile and water

Sources & evidence

ORD record
ord-43942d430aa84f388807f25cab9961da
Source dataset
uspto-grants-2012_03
Patent number
US08129557B2

Reaction notes

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