Trifluoroacetic acid → HCID 86697154, compound

HRID 471450Notes

Reaction equation

HRID 471450 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][O:13][C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([Br:21])=[C:16]([CH3:22])[CH:15]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[Br:21][C:17]1[C:18]([CH3:20])=[CH:19][C:14]([O:13][CH2:12][CH:10]2[CH2:11][NH:8][CH2:9]2)=[CH:15][C:16]=1[CH3:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86697155HCID 86697155, compound

Product 1

HCID 86697154HCID 86697154, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(4-Bromo-3,5-dimethyl-phenoxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (3.9 g, 6.32 mmol) is dissolved in 30 mL of dichloromethane and stirred at 0° C. Trifluoroacetic acid (1.45 g, 12.64 mmol) is added and the reaction mixture is stirred at 0° C. for 6 h. 15 mL of saturated aqueous NaHCO3 is added, the organic phase is separated, dried over sodium sulfate and concentrated under vacuum to give the title compound (Yield: 1.30 g).

Workup

  1. stirringthe reaction mixture is stirred at 0° C. for 6 h
  2. customthe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-51cf3e934ee543a9a4e7b075fbc12029
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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