Trifluoroacetic acid → HCID 22928682, compound

HRID 1453915Notes

Reaction equation

HRID 1453915 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([CH:15]1[CH:19]([CH2:20][CH2:21][CH3:22])[CH2:18][N:17](C(OC(C)(C)C)=O)[C:16]1=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(Cl)Cl>[CH2:8]([CH:15]1[CH:19]([CH2:20][CH2:21][CH3:22])[CH2:18][NH:17][C:16]1=[O:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22928671HCID 22928671, compound

Product 1

HCID 22928682HCID 22928682, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added to a solution of tert-butyl 3-benzyl-2-oxo-4-propyl-1-pyrrolidinecarboxylate (1.22 g, 3.84 mmol) in methylene chloride (10 ml) while cooling on ice and the mixture was stirred for 14 hours. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture and extraction was performed with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to yield a crude product of the title compound (0.83 g) as white crystals. 1H-NMR (CDCl3) δ(ppm) 0.79 (3H, t, J=7.2 Hz), 1.08-1.36 (4H, m), 2.04-2.21 (1H, m), 2.28-2.40 (1H, m), 2.81-2.96 (2H, m), 3.09 (1H, dd, J=14.0 Hz, 4.8 Hz), 3.29 (1H, dd, J=8.4 Hz, 8.4 Hz), 5.73 (1H, brs), 7.15-7.36 (5H, m)

Workup

  1. temperaturewhile cooling on ice
  2. washAfter washing the organic layer with brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-15a394835b11496ba1aec30c12dad121
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Reaction notes

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