HCID 18403070, compound → HCID 9903422, compound

HRID 1003169Notes

Reaction equation

HRID 1003169 reaction equation
[CH2:1]([P:5]([CH2:8][CH:9]([C:22]([O:24]CC1C=CC=CC=1)=[O:23])[CH2:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])(=[O:7])[OH:6])[CH2:2][CH2:3][CH3:4]>O>[CH2:1]([P:5]([CH2:8][CH:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:22]([OH:24])=[O:23])([OH:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 18403070HCID 18403070, compound

Product 1

HCID 9903422HCID 9903422, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Butyl[2,4-di(benzyloxycarbonyl)butyl]phosphinic acid (2.9 g, 6.5 mmol) in 30 mL of water containing 0.32 g 10% Pd/C was hydrogenated on a Parr hydrogenator at 40 psi for 4.5 hours. The mixture was filtered through a pad of Celite and evaporated under high vacuum to give 2-[(butylhydroxyphosphinyl)methyl]pentanedioic acid (4, R=n-butyl) (0.75 g, 43%) as a clear and colorless viscous oil. 1H NMR (D2O): 2.4 ppm (m, 1H), 2.1 ppm (t, 2H), 1.9 ppm (m, 1H), 1.6 ppm (m, 3H), 1.4 ppm (m, 2H), 1.1 ppm (m, 4H), 0.6 ppm (t, 3H) Elemental Analysis Calculated C10H19O6P. 0.5 H2O: C 43.64, H 7.32: Found C 43.25, H 7.12

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customevaporated under high vacuum

Sources & evidence

ORD record
ord-54eb03ef77d8497cb3eb9d78dc3a0dd6
Source dataset
uspto-grants-2000_04
Patent number
US06046180

Reaction notes

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