Dichloromethane → HCID 57879620, compound

HRID 1673560Notes

Reaction equation

HRID 1673560 reaction equation
FC(F)(F)C(O)=O.C(Cl)Cl.[C:11]([NH:19][C:20]1[CH:21]=[C:22]([CH:40]=[CH:41][C:42]=1[C:43]([O:45]C(C)(C)C)=[O:44])[O:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29](C(OC(C)(C)C)=O)[CH:28]=[CH:27]2)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:11]([NH:19][C:20]1[CH:21]=[C:22]([O:23][C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][CH:28]=[CH:27]3)[CH:40]=[CH:41][C:42]=1[C:43]([OH:45])=[O:44])(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67345346HCID 67345346, compound

Product 1

HCID 57879620HCID 57879620, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.0 mL of trifluoroacetic acid was added to 4.0 mL of methylene chloride solution containing the obtained tert-butyl 5-(3-(benzamido)-4-(tert-butoxycarbonyl)phenoxy)-1H-indole-1-carboxylate while ice-cooled and stirred at the same temperature for 2 hours and 30 minutes. After the reaction mixture was warmed to room temperature, ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added. The aqueous layer was separated and washed with ethyl acetate after adjusted to pH 6.5 with 6.0 mol/L hydrochloric acid and allowed to stand still for 17 hours. A solid substance was separated by filtration to obtain 10 mg of 2-(benzamido)-4-(1H-indol-5-yloxy)benzoic acid as white solid.

Workup

  1. temperaturecooled
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate after adjusted to pH 6.5 with 6.0 mol/L hydrochloric acid
  4. waitto stand still for 17 hours
  5. customA solid substance was separated by filtration

Sources & evidence

ORD record
ord-a24c50d084ff4aa48fdc3a1bb3f5ecd3
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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