Dimethylamine → Bis(2,2,2-trifluoroethyl) 2-(dimethylamino)-2-oxoethylphosphonate

HRID 1959161Notes

Reaction equation

HRID 1959161 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][P:5]([CH2:13][C:14](O)=[O:15])([O:7][CH2:8][C:9]([F:12])([F:11])[F:10])=[O:6].[N:19]1[CH:24]=CC=C[CH:20]=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.CNC>C(OCC)(=O)C>[CH3:20][N:19]([CH3:24])[C:14](=[O:15])[CH2:13][P:5](=[O:6])([O:7][CH2:8][C:9]([F:12])([F:11])[F:10])[O:4][CH2:3][C:2]([F:18])([F:17])[F:1]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 10870416Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-

Product 1

HCID 53663451Bis(2,2,2-trifluoroethyl) 2-(dimethylamino)-2-oxoethylphosphonateYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Bis-(2,2,2-trifluoroethyl)phosphonoacetic acid (0.07 mol) was dissolved in 100 ml of ethyl acetate. To this solution 5.6 g of pyridine (0.07 mol) were added, followed by 20.4 g (0.093 mol) of Boc anhydride. The mixture was stirred for 15 min and anhydrous dimethylamine (0.07 mol) was added. The mixture was stirred overnight. The mixture was stirred for 1 h at 5° C., and worked-up. Following distillation bis(2,2,2-trifluoroethyl) 2-(dimethylamino)-2-oxoethylphosphonate was obtained in 80% yield.

Workup

  1. stirringThe mixture was stirred overnight
  2. stirringThe mixture was stirred for 1 h at 5° C.
  3. distillationdistillation bis(2,2,2-trifluoroethyl) 2-(dimethylamino)-2-oxoethylphosphonate
  4. customwas obtained in 80% yield

Sources & evidence

ORD record
ord-a6819e3f2998498bb36b0c710b53bddd
Source dataset
uspto-grants-2013_04
Patent number
US08410176B2

Reaction notes

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