Dibenzyl 2,2-di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonate → 2,2-Di{4-[difluoro(phosphono)methyl]benzyl}malonic acid, dibenzyl ester

HRID 566495Notes

Reaction equation

HRID 566495 reaction equation
C([O:5][P:6]([C:13]([F:65])([F:64])[C:14]1[CH:63]=[CH:62][C:17]([CH2:18][C:19]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([P:50]([O:57]C(C)(C)C)([O:52]C(C)(C)C)=[O:51])([F:49])[F:48])=[CH:43][CH:42]=2)([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[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:65][C:13]([F:64])([P:6]([OH:8])([OH:7])=[O:5])[C:14]1[CH:15]=[CH:16][C:17]([CH2:18][C:19]([CH2:40][C:41]2[CH:42]=[CH:43][C:44]([C:47]([F:48])([F:49])[P:50]([OH:57])([OH:52])=[O:51])=[CH:45][CH:46]=2)([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])=[CH:62][CH:63]=1

Participants

3

Reactant 1

HCID 21265761Dibenzyl 2,2-di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonate

Product 1

HCID 154858912,2-Di{4-[difluoro(phosphono)methyl]benzyl}malonic acid, dibenzyl esterYield 131%

Reagents, catalysts & solvents 1

HCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of dibenzyl 2,2-di{4-[(di-tert-butoxyphosphoryl) (difluoro)methyl]benzyl}malonate (100 mg) in 2 mL of 10:1 TFA/water was stirred for 0.5 h and then concentrated. The residue was dissolved in 5 mL of water and lyopholized to give 100 mg of the title compound as a beige solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 5 mL of water

Sources & evidence

ORD record
ord-01e63c3d0a634c03967e7e761b22367b
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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