Triethylamine → (2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

HRID 1349001Notes

Reaction equation

HRID 1349001 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.[CH3:18][O:19][NH2:20].C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[N:20][O:19][CH3:18])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

Product 1

HCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acidYield 97.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution was made containing (2S)-1-(tert-butoxycarbonyl)-4-oxo-2-pyrrolidinecarboxylic acid (5.0 g, 21 mmol) and O-methylhydroxylamine hydrochloride (2.7 g, 32.8 mmol) in chloroform (100 ml) containing triethylamine (5.5 g, 55 mmol). The reaction mixture was then stirred at ambient temperature overnight, prior to removal of solvent. The resultant crude reaction mixture was dissolved in ethyl acetate (150 ml) and washed rapidly with 1N 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 (5.3 g, 94%) was isolated as a pale yellow oil.

Workup

  1. customto removal of solvent
  2. customThe resultant crude reaction mixture
  3. washwashed rapidly with 1N HCl (40 ml)
  4. extractionThe acidic layer was then extracted with ethyl acetate (3×20 ml)
  5. washthe combined organic layers washed with brine
  6. dry with materialbefore drying over magnesiom sulfate
  7. filtrationfiltering
  8. customremoval of solvent in vacuo

Sources & evidence

ORD record
ord-d167db5d04024d89a180e4b3afbdc462
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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