Trifluoroacetic acid → HCID 67532753, compound

HRID 1713073Notes

Reaction equation

HRID 1713073 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[S:30][C:18]2[N:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20](=[O:23])[CH:21]=[CH:22][C:17]=2[C:16]=1[C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=1)(C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:14][C:15]1[S:30][C:18]2[N:19]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:20](=[O:23])[CH:21]=[CH:22][C:17]=2[C:16]=1[C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131728321HCID 131728321, compound

Product 1

HCID 67532753HCID 67532753, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 ml) was added to a solution of Example 3 (5.4 g, 11.0 mmol) in DCM (20 ml) and stirred at r.t. for 5 h. NaHCO3(aq) (200 ml) was added to the reaction, and the mixture extracted with DCM (3×100 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography (silica, 10% THF in DCM) to give the title compound as a yellow solid (3.0 g, 76%). δH (CDCl3) 7.52-7.45 (3H, m), 7.33-7.30 (6H, m), 6.72 (1H, d, J 9.6 Hz), 6.33 (1H, d, J 9.6 Hz), 2.35 (3H, s). LCMS (ES+) RT 3.11 minutes, 361 (M+H)+.

Workup

  1. extractionthe mixture extracted with DCM (3×100 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by chromatography (silica, 10% THF in DCM)

Sources & evidence

ORD record
ord-e6de6caae22444d4b81129cba929e99d
Source dataset
uspto-grants-2010_09
Patent number
US07795256B2

Reaction notes

Loading…