Trifluoroacetic acid → HCID 21083983, compound

HRID 347913Notes

Reaction equation

HRID 347913 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13]2[S:21][C:22]([NH:30]C(=O)OC(C)(C)C)=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:12]=2[CH:11]=[CH:10]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:30][C:22]1[S:21][C:13]2[N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9](=[O:8])[CH:10]=[CH:11][C:12]=2[C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21084092HCID 21084092, compound

Product 1

HCID 21083983HCID 21083983, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a solution of the compound of Example 80 (170 mg, 0.406 mmol) in DCM (2 mL) and the reaction mixture stirred for 2 h at r.t. The mixture was added to saturated NaHCO3(aq) (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 flash column chromatography on silica (EtOAc), followed by radial chromatography (20% EtOH in DCM) to give the title compound as a buff solid (30 mg, 23%). δH (CDCl3) 7.8–7.3 (13H, m), 6.58 (1H, d, J 9 Hz). m/z (ES+) 319 (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 flash column chromatography on silica (EtOAc)

Sources & evidence

ORD record
ord-67395c5ea62645ed8fb0781586c41261
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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