2,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}-3-methoxy-3-oxopropanoic acid → 2,2-Di{4-[difluoro(phosphono)methyl]benzyl}-3-methoxy-3-oxopropanoic acid

HRID 566497Notes

Reaction equation

HRID 566497 reaction equation
C([O:5][P:6]([C:13]([F:52])([F:51])[C:14]1[CH:50]=[CH:49][C:17]([CH2:18][C:19]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]([P:37]([O:44]C(C)(C)C)([O:39]C(C)(C)C)=[O:38])([F:36])[F:35])=[CH:30][CH:29]=2)([C:23]([O:25][CH3:26])=[O:24])[C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1)([O:8]C(C)(C)C)=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O.O>[F:52][C:13]([F:51])([P:6]([OH:8])([OH:7])=[O:5])[C:14]1[CH:50]=[CH:49][C:17]([CH2:18][C:19]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]([F:35])([F:36])[P:37]([OH:44])([OH:39])=[O:38])=[CH:32][CH:33]=2)([C:23]([O:25][CH3:26])=[O:24])[C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1

Participants

3

Reactant 1

HCID 212657292,2-Di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}-3-methoxy-3-oxopropanoic acid

Product 1

HCID 212657222,2-Di{4-[difluoro(phosphono)methyl]benzyl}-3-methoxy-3-oxopropanoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of 2,2-di{4-[(di-tert-butoxyphosphoryl) (difluoro)methyl]benzyl}-3-methoxy-3-oxopropanoic acid(80 mg) in 5 mL of 10:1 TFA/water was stirred for 1 h and then concentrated. The residue was dissolved in 4 mL of water and washed with 2×5 mL of ether and the aqueous solution was lyopholized to give 20 mg of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 4 mL of water
  3. washwashed with 2×5 mL of ether

Sources & evidence

ORD record
ord-3e2b90b898cf4c7ead6d148224f64fda
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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