Trifluoroacetic acid → HCID 90412344, compound

HRID 1521993Notes

Reaction equation

HRID 1521993 reaction equation
[Cl:1][C:2]1[C:3]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][N:14]([C:17](OC(C)(C)C)=O)[CH2:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.F[C:34](F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH3:34])[CH2:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90411711HCID 90411711, compound

Product 1

HCID 90412344HCID 90412344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 229E (0.072 g, 0.157 mmol) in dichloromethane (1.429 mL) was treated with 2,2,2-trifluoroacetic acid (0.121 mL, 1.572 mmol) and the mixture was stirred at room temperature for 8 hours. The mixture was concentrated and the residue was partitioned in ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was back-extracted with additional ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to provide the title compound. MS (ESI+) m/z 358.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned in ethyl acetate
  3. extractionThe aqueous layer was back-extracted with additional ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-08a04941454b4b8b81eb3294ba10e99b
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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