Trifluoroacetic acid → HCID 65439120, compound

HRID 2041894Notes

Reaction equation

HRID 2041894 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:20])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:20])[CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 659188071,1-Dimethylethyl 3-(3,4-difluorophenyl)-3-hydroxy-1-azetidinecarboxylate

Product 1

HCID 65439120HCID 65439120, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 3-(3,4-difluorophenyl)-3-hydroxyazetidine-1-carboxylate (1.06 g, 3.72 mmol) and trifluoroacetic acid (3 ml) in dichloromethane (30 ml) was stirred at ambient temperature for 1.5 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) to give the title compound (0.52 g). MS m/z (rel. intensity, 70 eV) 185 (M+, 1), 156 (50), 141 (bp), 127 (58), 114 (90).

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)

Sources & evidence

ORD record
ord-154574165eac406c87b3cc9c5dc9d2b6
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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