Dibenzyl 2-((bis(benzyloxy)phosphoryl)methyl)pentanedioate → 2-(phosphonomethyl)pentanedioic acid

HRID 612367Notes

Reaction equation

HRID 612367 reaction equation
C([O:8][P:9]([CH2:19][CH:20]([CH2:31][CH2:32][C:33]([O:35]CC1C=CC=CC=1)=[O:34])[C:21]([O:23]CC1C=CC=CC=1)=[O:22])([O:11]CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1>[Pd].CO>[P:9]([CH2:19][CH:20]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:21]([OH:23])=[O:22])([OH:11])([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 15295730Dibenzyl 2-((bis(benzyloxy)phosphoryl)methyl)pentanedioate

Product 1

HCID 101307542-(phosphonomethyl)pentanedioic acidYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The benzyl pentanedioate 2(2.9 g, 4.9 mmol) was added to a mixture of 20 ml of methanol containing 0.29 g (6 mol %) of 10% Pd/C. This mixture was hydrogenated on a Parr hydrogenator at 40 psi for 24 hours, filtered and evaporated to give 3(1.0 g, 90%) as a clear slightly golden viscous oil.

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-6e298782d2fd496196f5ea4130a76a30
Source dataset
uspto-grants-1999_12
Patent number
US06004946

Reaction notes

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