1,2-Dichloroethane → HCID 86608818, compound

HRID 2055579Notes

Reaction equation

HRID 2055579 reaction equation
[Cl-].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH3+:11])[CH3:10])=[C:5]([F:12])[CH:4]=1.[F:13][C:14]([F:25])([F:24])[C:15]([NH:17][C:18]1([C:21](O)=[O:22])[CH2:20][CH2:19]1)=[O:16].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C)C=O.O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH:11][C:21]([C:18]2([NH:17][C:15](=[O:16])[C:14]([F:13])([F:24])[F:25])[CH2:19][CH2:20]2)=[O:22])[CH3:10])=[C:5]([F:12])[CH:4]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 129888001-(2,2,2-Trifluoroacetamido)cyclopropane-1-carboxylic acidHCID 86590342HCID 86590342, compound

Product 1

HCID 86608818HCID 86608818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(1R)-1-(4-Bromo-2-fluorophenyl)ethanaminium chloride (16.50 g, 64.83 mmol), 1-[(trifluoroacetyl)amino]cyclopropanecarboxylic acid (12.78 g, 64.83 mmol), EDC (12.43 g, 64.83 mmol), and HOAT (4.41 g, 32.41 mmol) were dissolved in dimethylformamide (100 mL). To this solution was added triethylamine (6.56 g, 64.83 mmol). After 6 hours, the reaction was diluted with water and extracted with ethyl acetate. The organic extract was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to yield a solid. This solid was purified by silica gel chromatography and eluted with 5% methanol/CH2Cl2 to yield N-[(1R)-1-(4-bromo-2-fluorophenyl)ethyl]-1-[(trifluoroacetyl)amino]cyclopropanecarboxamide as a white solid. Low resolution mass spectrometry: (M+H+)=399.0.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a solid
  8. customThis solid was purified by silica gel chromatography
  9. washeluted with 5% methanol/CH2Cl2

Sources & evidence

ORD record
ord-5ec7d7d79c914d5e924500bb8797ff53
Source dataset
uspto-grants-2008_02
Patent number
US07332499B2

Reaction notes

Loading…