Trifluoroacetic acid → 1202890-94-5

HRID 1021546Notes

Reaction equation

HRID 1021546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:18][CH3:19])[CH2:9][NH:10]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:18][CH3:19])[CH2:9][NH2:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080810HCID 67080810, compound

Product 1

HCID 532762401202890-94-5Yield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(4-chlorophenyl)-2-methoxyethylcarbamate (0.129 g, 0.451 mmol) in dichloromethane (5 ml) was added trifluoroacetic acid (5 ml), and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated and taken up in water. Sodium hydroxide (1M) was added until the pH was >13. The mixture was extracted twice with dichloromethane, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to yield 71 mg of the title compound (84.7% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. additionSodium hydroxide (1M) was added until the pH was >13
  3. extractionThe mixture was extracted twice with dichloromethane
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-146b2d051d4240efb0d695b8acd43309
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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