Trifluoroacetic acid → HCID 91690193, compound

HRID 2206554Notes

Reaction equation

HRID 2206554 reaction equation
[CH3:1][C:2]1[N:3]([C:18](=[O:23])[CH2:19][CH:20]([CH3:22])[CH3:21])[C:4]2[C:9]([C:10]=1[C:11]([O:13]C(C)(C)C)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[N:3]([C:18](=[O:23])[CH2:19][CH:20]([CH3:21])[CH3:22])[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117778922HCID 117778922, compound

Product 1

HCID 91690193HCID 91690193, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl 2-methyl-1-(3-methylbutanoyl)-1H-indole-3-carboxylate (200 mg, 634.10 μmol) in dichloromethane (5 mL) was added trifluoroacetic acid (5 mL). The mixture was stirred at room temperature (25° C.) for 1 hour. The mixture was evaporated and partitioned between dichloromethane and water. The aqueous layer was washed with dichloromethane (10 mL×2), combined the organic layers, dried over sodium sulfate, then filtered and concentrated in vacuum afford the title compound (30 mg, yield: 89%).

Workup

  1. customThe mixture was evaporated
  2. custompartitioned between dichloromethane and water
  3. washThe aqueous layer was washed with dichloromethane (10 mL×2)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-8353ab0887974c1e83d5bde2720d4563
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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