HCID 15885218, compound → HCID 10198410, compound

HRID 1003167Notes

Reaction equation

HRID 1003167 reaction equation
C([O:8][C:9]([CH:11]([CH2:24][CH2:25][C:26]([O:28]CC1C=CC=CC=1)=[O:27])[CH2:12][P:13]([CH3:23])(=[O:22])[O:14]CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1>O.[Pd]>[CH3:23][P:13]([CH2:12][CH:11]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:9]([OH:10])=[O:8])([OH:22])=[O:14]

Participants

4

Reactant 1

HCID 15885218HCID 15885218, compound

Product 1

HCID 10198410HCID 10198410, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2,4-di(benzyloxycarbonyl)buty(methyl)-O-benzylphosphinic acid (0.8 g, 1.6 mmol) in 20 mL of water containing 100 mg of 10% Pd/C was hydrogenated at 40 psi for 4 hours. The mixture was filtered over a pad of Celite and evaporated at high vacuum to give 2-[(methylhydroxyphosphinyl)methyl]pentanedioic acid (4,R=CH3,0.28 g, 78% as a clear and colorless viscous oil. 1H NMR (D2O): 2.5 ppm(m,1H), 2.2 ppm(t,2H), 2.0 ppm (m,1H), 1.7 ppm(m,3H), 1.3 ppm (d, 3H) Elemental Analysis Calculated C7H13O6P.0.2 H2O: C36.92 H 5.93 Found: C37.06 H 6.31

Workup

  1. filtrationThe mixture was filtered over a pad of Celite
  2. customevaporated at high vacuum

Sources & evidence

ORD record
ord-829d9782378845faaf6addb0a3fa401f
Source dataset
uspto-grants-2000_04
Patent number
US06046180

Reaction notes

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