Trifluoroacetic acid → HCID 21084085, compound

HRID 347915Notes

Reaction equation

HRID 347915 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9]([N:12]([C:20]1[S:35][C:23]2[N:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:25](=[O:28])[CH:26]=[CH:27][C:22]=2[C:21]=1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)C(=O)OC(C)(C)C)(=[O:11])=[O:10].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:28]=[C:25]1[N:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[S:35][C:20]([NH:12][S:9]([CH3:8])(=[O:11])=[O:10])=[C:21]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:22]=2[CH:27]=[CH:26]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21084093HCID 21084093, compound

Product 1

HCID 21084085HCID 21084085, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.5 mL) was added to a solution of the compound of Example 82 (105 mg, 0.212 mmol) in DCM (2.5 mL) and the reaction mixture stirred for 2 h at r.t. The mixture was added to saturated NaHCO3 solution (20 mL) and the product extracted with DCM (2×20 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by radial chromatography on silica (EtOAc) to give the title compound (62 mg, 74%). δH (CDCl3) 7.6–7.25 (11H, m), 6.58 (1H, d, J 9 Hz), 6.31 (1H, br s), 2.53 (3H, s). m/z (ES+) 397 (M+H)+.

Workup

  1. extractionthe product extracted with DCM (2×20 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by radial chromatography on silica (EtOAc)

Sources & evidence

ORD record
ord-475c15a443f8438cad06e3e14262c4ca
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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