Trifluoroacetic acid → HCID 86648968, compound

HRID 449935Notes

Reaction equation

HRID 449935 reaction equation
C(OC([NH:8][CH:9]1[CH2:12][CH:11]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH:9]1[CH2:12][CH:11]([O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86648967HCID 86648967, compound

Product 1

HCID 86648968HCID 86648968, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzoic acid 3-tert-butoxycarbonylaminocyclobutyl ester (100 mg, 0.34 mmol) in DCM (2 mL) was added TFA (2 mL). The reaction mixture was stirred at room temperature for 2 hrs and then concentrated under reduced pressure. The residue was partitioned between EtOAc (20 mL) and saturated aqueous sodium hydrogenocarbonate solution (20 mL). The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give benzoic acid 3-aminocyclobutyl ester as a colorless oil (62 mg, yield: 94%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc (20 mL) and saturated aqueous sodium hydrogenocarbonate solution (20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60ff9fd3a8c34b68a2b17049713b6d7c
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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