2,2,2-Trifluoroacetophenone → N-(2,2,2-Trifluoro-1-phenylethylidene)-L-valine potassium salt

HRID 351303

Reaction equation

HRID 351303 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O:15][C:16](=[O:22])[C@H:17]([CH:19]([CH3:21])[CH3:20])[NH2:18])C.C([O-])([O-])=O.[K+:27].[K+]>CO>[K+:27].[F:1][C:2]([F:12])([F:11])[C:3](=[N:18][C@H:17]([C:16]([O-:22])=[O:15])[CH:19]([CH3:21])[CH3:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 99052,2,2-TrifluoroacetophenoneHCID 11430Potassium CarbonateHCID 87182l-Valine, ethyl ester

Product 1

HCID 58599713N-(2,2,2-Trifluoro-1-phenylethylidene)-L-valine potassium salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

2,2,2-Trifluoroacetophenone (4.24 g, 24.3 mmol) was added to a mixture of L-valine ethyl ester (3.21 g, 22.1 mmol) and K2CO3 (2.90 g, 20.9 mmol) in MeOH (50 mL). The mixture was warmed to 50° C. for 18 h. The mixture was cooled to 20–25° C., filtered and concentrated. The residue was suspended in TBME (100 ml) and filtered to give the title compound as a white solid.

Workup

  1. temperatureThe mixture was cooled to 20–25° C.
  2. filtrationfiltered
  3. concentrationconcentrated
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9b16be21d1324a09bd32db5352ab2673
Source dataset
uspto-grants-2007_02
Patent number
US07183425B2

Linked notes

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