Trifluoroacetic acid → HCID 46208244, compound

HRID 2041890Notes

Reaction equation

HRID 2041890 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:20][CH3:21])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([O:20][CH3:21])[CH2:12][NH:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66995363HCID 66995363, compound

Product 1

HCID 46208244HCID 46208244, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(2,3-difluorophenyl)-3-methoxyazetidine-1-carboxylate (0.7 g, 2.34 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (3 ml, 40 mmol). The resulting mixture was stirred at ambient temperature for 2 h. The solvent was evaporated and the crude product was purified on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1). The solvents where evaporated to give (0.16 g, 64%) of the title compound. The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 141-142° C. MS m/z (relative intensity, 70 eV) 199 (M+, 1), 170 (bp), 169 (97), 140 (82), 127 (47).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)
  3. customThe solvents where evaporated

Sources & evidence

ORD record
ord-307d3c8db290418f8e01279314285f56
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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