Trifluoroacetic acid → HCID 66990568, compound

HRID 454510Notes

Reaction equation

HRID 454510 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]1[CH:35]=[CH:34][C:33]([CH:36]2[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]2)=[CH:32][C:17]=1[C:18]([NH:20][C:21]1[CH:30]=[C:29]([Br:31])[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:8]([O:15][C:16]1[CH:35]=[CH:34][C:33]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)=[CH:32][C:17]=1[C:18]([NH:20][C:21]1[CH:30]=[C:29]([Br:31])[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66990686HCID 66990686, compound

Product 1

HCID 66990568HCID 66990568, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, trifluoroacetic acid (1.3 mL) was added to a methylene chloride (6.5 mL) solution of methyl 2-(2-(benzyloxy)-5-(1-(tert-butoxycarbonyl)piperidin-4-yl)benzamido)-4-bromobenzoate (0.65 g), followed by stirring at room temperature for 30 minutes. The reaction mixture was added to a saturated aqueous solution of sodium bicarbonate under ice-cooling. The organic layer was separated, washed with a saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 0.54 g of methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-bromobenzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1d1b75c4583b4c37b1ac09705b4ff7c1
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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