Trifluoroacetic acid → 2,2,2-trifluoro-N-(6-isopropoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide

HRID 501734Notes

Reaction equation

HRID 501734 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]([CH3:16])[CH3:15])[CH:8]=1)[CH2:3][C:4]([OH:6])=O.[C:17](O)([C:19]([F:22])([F:21])[F:20])=[O:18].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.CCOC(C)=O>O>[F:20][C:19]([F:22])([F:21])[C:17]([NH:1][CH:2]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([O:13][CH:14]([CH3:16])[CH3:15])[CH:8]=2)[C:4](=[O:6])[CH2:3]1)=[O:18]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 230026273-Amino-3-(3-isopropoxyphenyl)propanoic acid

Product 1

HCID 866223552,2,2-trifluoro-N-(6-isopropoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamideYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Step AU (3). To a solution of 3-amino-3-(3-isopropoxyphenyl)propanoic acid (65 g, 291 mmol) and TFA (100 mL) was added TFAA (100 mL). The mixture was warmed up to 95° C. for 2 h. The solvent was evaporated under high vacuum to afford a sticky oil which was taken into EtOAc (500 mL) and water (300 mL). The organic layer was separated, dried over Na2SO4, and concentrated in vacuo. The residue was purified using silica-gel chromatography (10-30% EtOAc/Hexane) to afford 20 g (23% yield) of 2,2,2-trifluoro-N-(6-isopropoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide as a white solid.

Workup

  1. customThe solvent was evaporated under high vacuum
  2. customto afford a sticky oil which
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-f189131343fb40afa5c7fcc3f6d371d7
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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