Trifluoroacetic acid → (2S,5R)-5-(Benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylic acid

HRID 711001Notes

Reaction equation

HRID 711001 reaction equation
[CH2:1]([O:8][NH:9][C@H:10]1[CH2:15][N:14]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C@H:13]([C:22]([O:24]C(C)(C)C)=[O:23])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][NH:9][C@H:10]1[CH2:15][N:14]([C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[C@H:13]([C:22]([OH:24])=[O:23])[CH2:12][CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57389515(2S,5R)-tert-Butyl 5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate

Product 1

HCID 87217278(2S,5R)-5-(Benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylic acidYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2S,5R)-tert-Butyl 5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate (1.50 g, 3.73 mmol) in methylene chloride (5.0 mL) was ice-cooled, and trifluoroacetic acid (5.0 mL) was added, and reacted at the same temperature for 30 min. and then at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure, then water and 6.5% sodium bicarbonate aqueous solution was added to the residue. After pH was adjusted to ca. pH 8, aqueous layer was washed with ethyl acetate. To this aqueous layer was added 5% potassium hydrogen sulfate aqueous solution. After pH was adjusted to ca. pH 5.6, the aqueous layer was extracted with ethyl acetate. After the organic layer was washed with saturated brine, dehydrated over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to afford 0.913 g of the title compound (yield 71%).

Workup

  1. temperaturecooled
  2. customreacted at the same temperature for 30 min.
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionwater and 6.5% sodium bicarbonate aqueous solution was added to the residue
  5. washwas washed with ethyl acetate
  6. additionTo this aqueous layer was added 5% potassium hydrogen sulfate aqueous solution
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washAfter the organic layer was washed with saturated brine
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8e5a0ad0c07740b7adc89d0ae36900a1
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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