HCID 18403062, compound → HCID 178527042, compound

HRID 1003171Notes

Reaction equation

HRID 1003171 reaction equation
[CH2:1]([P:8](CC(C(OCC1C=CC=CC=1)=O)CCC(OCC1C=CC=CC=1)=O)(=[O:10])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.[Pd]>[CH2:1]([PH:8](=[O:9])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18403062HCID 18403062, compound

Product 1

HCID 178527042HCID 178527042, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Benzyl[2,4-di(benzyloxycarbonyl)butyl]phosphinic acid(0.5 g, 1.0 mmol) in 20 mL of water containing 120 mg of 10% Pd/C was hydrogenated on a Parr hydrogenator at 40 psi for 6 hours. Filtration through a Celite pad followed by evaporation on high vacuum gave 0.17 g (57%) of 2-[(benzylhydroxyphosphinyl)methyl]pentanedioic acid(4,R=CH2Ph) as a white solid. 1H NMR (D2O): 7.1 ppm(m,5H), 2.9 ppm(d,2H), 2.4 ppm(m,1H), 2.1 ppm(t,2H), 1.8 ppm(m,1H), 1.6 ppm(m,3H) Elemental Analysis, Calculated C13H17O6P: C52.00H5.71: Found: C51.48H5.70

Workup

  1. filtrationFiltration through a Celite pad
  2. customfollowed by evaporation on high vacuum
  3. customgave 0.17 g (57%) of 2-[(benzylhydroxyphosphinyl)methyl]pentanedioic acid(4,R=CH2Ph) as a white solid

Sources & evidence

ORD record
ord-18de06b8c6684ab3be55b8b6adf7406d
Source dataset
uspto-grants-2000_04
Patent number
US06046180

Reaction notes

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