4-[(Dimethoxy-phosphoryl)fluoro-methyl]-benzoic acid benzyl ester → 4-[(Dimethoxy-phosphoryl)-fluoro-methyl]-benzoic acid

HRID 1013483Notes

Reaction equation

HRID 1013483 reaction equation
C([O:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]([P:18]([O:22][CH3:23])([O:20][CH3:21])=[O:19])[F:17])=[CH:12][CH:11]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:21][O:20][P:18]([CH:16]([F:17])[C:13]1[CH:14]=[CH:15][C:10]([C:9]([OH:24])=[O:8])=[CH:11][CH:12]=1)([O:22][CH3:23])=[O:19]

Participants

4

Reactant 1

HCID 579260124-[(Dimethoxy-phosphoryl)fluoro-methyl]-benzoic acid benzyl ester

Product 1

HCID 579258224-[(Dimethoxy-phosphoryl)-fluoro-methyl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring solution of 4-[(dimethoxy-phosphoryl)-fluoro-methyl]-benzoic acid benzyl ester (76 mg, 0.216 mmol) in MeOH (0.21M) was added 20 mol % Pd on Carbon (0.043 mmol). The resulting mixture was degassed with alternating vacuum and hydrogen gas (4×), then stirred under a hydrogen atmosphere (1 atm) at ambient temperature for 18 hours. The reaction mixture was filtered through a nylon syringe filter and concentrated in vacuo to give the title compound: MS: cal'd 263 (MH+), exp 263 (MH+)

Workup

  1. customThe resulting mixture was degassed
  2. filtrationThe reaction mixture was filtered through a nylon syringe
  3. filtrationfilter
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-463e561998c74524b591395012f3d018
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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