Trifluoroacetic acid → HCID 23103401, compound

HRID 499187Notes

Reaction equation

HRID 499187 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:30])[C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])[CH2:17][CH2:16]2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]([C:22]3[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])=[O:30])[CH2:19][CH2:20]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59420870{4-[1-(2,6-Dichloro-benzoyl)-piperidin-4-yloxy]-phenyl}-carbamic acid tert-butyl ester

Product 1

HCID 23103401HCID 23103401, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

The above white solid, {4-[1-(2,6-dichloro-benzoyl)-piperidin-4-yloxy]-phenyl}-carbamic acid tert-butyl ester, is suspended in a solution of trifluoroacetic acid in dichloromethane (25% v/v, 20 mL). The reaction mixture is stirred at 22° C. for 15 min. After removal of the solvent, the oily residue is neutralized with 0.5 N aqueous sodium hydroxide solution (50 mL) and extracted with dichloromethane (5×50 mL). The combined organic phases are dried over anhydrous sodium sulfate and concentrated to yield a yellow solid (440.2 mg, 92.0% yield, ES+(m/z) 365.1 [M+H]).

Workup

  1. customAfter removal of the solvent
  2. extractionextracted with dichloromethane (5×50 mL)
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto yield a yellow solid (440.2 mg, 92.0% yield, ES+(m/z) 365.1 [M+H])

Sources & evidence

ORD record
ord-a8eb332209a84b3aa709d5b81503900b
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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