Pyridine → (2S,4EZ)-1-(tertbutoxycarbonyl)-4-(ethoxyirnino)-2-pyrrolidinecarboxylic acid

HRID 1349002Notes

Reaction equation

HRID 1349002 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:18]([O:20][NH2:21])[CH3:19].N1C=CC=CC=1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[N:21][O:20][CH2:18][CH3:19])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

Product 1

HCID 58714540(2S,4EZ)-1-(tertbutoxycarbonyl)-4-(ethoxyirnino)-2-pyrrolidinecarboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution was made containing (2S)-1-(tert-butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylic acid (5.0 g, 22 mmol) and O-ethylhydroxylamine hydrochloride (6.4 g, 65.5 mmol) in a 1:1 mixture of pyridine and ethanol (100 ml). The reaction was heated to reflux for 2.5 h before cooling and removal of solvent. The residue was dissolved in ethyl acetate and washed rapidly with 1.3N HCl (40 ml). The acidic layer was then extracted with ethyl acetate (3×20 ml) and the combined organic layers washed with brine before drying over magnesiom sulfate, filtering and removal of solvent in vacuo. The desired product (5.5 g, 93%) was isolated as a pale yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2.5 h
  3. temperaturebefore cooling
  4. customremoval of solvent
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed rapidly with 1.3N HCl (40 ml)
  7. extractionThe acidic layer was then extracted with ethyl acetate (3×20 ml)
  8. washthe combined organic layers washed with brine
  9. dry with materialbefore drying over magnesiom sulfate
  10. filtrationfiltering
  11. customremoval of solvent in vacuo

Sources & evidence

ORD record
ord-7540886945f9415cbde64284b2a36636
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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