Trifluoroacetic acid → HCID 178499463, compound

HRID 2423305Notes

Reaction equation

HRID 2423305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:26]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])(=[O:30])=[O:29])=[CH:25][C:12]2[N:13]=[C:14]([CH3:24])[N:15](COCC[Si](C)(C)C)[C:11]=2[CH:10]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:26]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=2[Cl:38])(=[O:29])=[O:30])=[CH:25][C:12]2[N:13]=[C:14]([CH3:24])[NH:15][C:11]=2[CH:10]=1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59864823HCID 59864823, compound

Product 1

HCID 178499463HCID 178499463, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Under an N2 atmosphere, methyl 2-(3-chloro-4-(6-(2,4-dichlorophenylsulfonamido)-2-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-benzo[d]imidazol-5-yloxy)phenyl)acetate (0.245 g, 0.358 mmol) was dissolved in dichloromethane (4.0 mL). Trifluoroacetic acid (2.5 mL) was added and the reaction was allowed to stir overnight at room temperature. The reaction was diluted with ethyl acetate and saturated NaHCO3 (aq). The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting 0% to 7% methanol in dichloromethane, afforded the title compound. LC-MS ESI (pos.) m/z: 555.8 (M+H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washFlash column chromatography of the residue, eluting 0% to 7% methanol in dichloromethane

Sources & evidence

ORD record
ord-f83ea8c337b04f37849a139e20f7cd66
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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