HCID 18403163, compound → HCID 9949326, compound

HRID 1934336Notes

Reaction equation

HRID 1934336 reaction equation
C([O:8][C:9]([CH:11]([CH2:25][CH2:26][C:27]([O:29]CC1C=CC=CC=1)=[O:28])[CH2:12][P:13]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:15])[OH:14])=[O:10])C1C=CC=CC=1>[Pd].O>[C:19]1([CH2:18][CH2:17][CH2:16][P:13]([CH2:12][CH:11]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:9]([OH:10])=[O:8])([OH:15])=[O:14])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 18403163HCID 18403163, compound

Product 1

HCID 9949326HCID 9949326, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2,4-Di(benzyloxycarbonyl)butyl(3-phenylpropyl)-phosphinic acid (15) (1.4 g, 2.8 mmol) in 20 Ml of water containing 150 mg of 10% Pd/C was hydrogenated at 40 psi overnight. Filtration through a Celite pad followed by evaporation on high vacuum gave 0.8 g (89%) of 2-[(3-phenylpropylhydroxyphosphinyl)methyl]pentanedioic acid (4, R=CH2CH2CH2Ph) as a light yellow viscous oil.

Workup

  1. customwas hydrogenated at 40 psi overnight
  2. filtrationFiltration through a Celite pad
  3. customfollowed by evaporation on high vacuum

Sources & evidence

ORD record
ord-6ddefbfb62534880915525c7ff73b2d4
Source dataset
uspto-grants-2002_05
Patent number
US06384022B1

Reaction notes

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