Triethylamine → (2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid
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
Product 1
Reagents, catalysts & solvents 2
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 triethyl-amine (5.5 g, 55 mmol). The reaction mixture was then stirred at ambient temperature over-night, 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
- customto removal of solvent
- customThe resultant crude reaction mixture
- washwashed rapidly with 1N HCl (40 ml)
- extractionThe acidic layer was then extracted with ethyl acetate (3×20 ml)
- washthe combined organic layers washed with brine
- dry with materialbefore drying over magnesiom sulfate
- filtrationfiltering
- customremoval of solvent in vacuo
Sources & evidence
- ORD record
- ord-919dc9c46aba4f79b7d1fd54896e80fc
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07018988B2
Reaction notes
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