Trifluoroacetic acid → HCID 86622365, compound

HRID 501754Notes

Reaction equation

HRID 501754 reaction equation
C(O[C@H]1C2C(=CC(OCCC)=CC=2)[C@@H](N)C1)C=C.[NH2:19][CH:20]([C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[CH:26]=1)[CH2:21][C:22]([OH:24])=O.[C:33](O)([C:35]([F:38])([F:37])[F:36])=[O:34].FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[CH3:32][C:27]1[CH:28]=[C:29]([CH3:31])[CH:30]=[C:25]2[C:26]=1[C:22](=[O:24])[CH2:21][CH:20]2[NH:19][C:33](=[O:34])[C:35]([F:38])([F:37])[F:36]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 3652810β-Amino-3,5-dimethylbenzenepropanoic acidHCID 59423826(1S,3R)-3-(Allyloxy)-6-propoxy-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 86622365HCID 86622365, compoundYield 71%

Procedure

Step BM (1). A solution of 3-amino-3-(3,5-dimethylphenyl)propanoic acid (18 g, 0.078 mol) and TFA (72 mL) was stirred at rt for 30 min. Trifluoroacetic anhydride (72 mL) was added and the resulting mixture was heated at reflux for 2 h. After cooling to rt, the reaction was concentrated in vacuo. The crude residue was dissolved in EtOAc and sequentially washed with 1 N NaOH and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford 15 g (71% yield) of N-(4,6-dimethyl-3-oxo-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide as a white solid. LC-MS (M+H)+=272.09; 1H NMR (500 MHz, CDCl3) δ ppm 7.17 (s, 1H) 7.04 (s, 1H) 6.91 (d, J=6.71 Hz, 1H) 5.52-5.59 (m, 1H) 3.15 (dd, J=18.92, 7.93 Hz, 1H) 2.50 (s, 3H) 2.46 (d, J=3.36 Hz, 1H) 2.40 (s, 3H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationthe reaction was concentrated in vacuo
  4. dissolutionThe crude residue was dissolved in EtOAc
  5. washsequentially washed with 1 N NaOH and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6db9d47d83d843af82f2bd9d1e4d460c
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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