Hydrochloric Acid → HCID 67459915, compound
Reaction equation
[CH2:1]([N:3]1[CH:7]([CH2:8][OH:9])[CH2:6][CH:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]1=[O:17])[CH3:2].[OH:18]P([O-])(O)=O.[Na+].CC1(C)N([O])C(C)(C)CCC1.Cl([O-])=O.[Na+].Cl[O-].[Na+].ClCl.S([O-])([O-])=O.[Na+].[Na+].Cl>C(#N)C>[CH2:1]([N:3]1[C:4](=[O:17])[CH:5]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C@H:7]1[C:8]([OH:18])=[O:9])[CH3:2]Participants
Reactant 8
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
1-Ethyl-5-(hydroxymethyl)-3-(phenylmethyl)-2-pyrrolidinone (0.748 g, 3.21 mmol) was dissolved in acetonitrile (5 ml) and a 1M aqueous sodium phosphate monobasic buffer solution (3.69 ml, 3.69 mmol), a few crystals of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy free radical), and sodium chlorite (0.580 g, 6.41 mmol) were added and the mixture was warmed to 40° C. Approximately 1 drop of bleach (sodium hypochlorite solution, available chlorine >12%) was then added to the mixture and stirring continued at 40° C. for 3 hrs. The mixture was then poured onto ice-water containing 1% w/w sodium sulphite and the resulting mixture was adjusted to pH2 using 5N aqueous hydrogen chloride and then extracted with ethyl acetate (×3). The combined organic extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulphate and concentrated to give 1-ethyl-5-oxo-4-(phenylmethyl)proline (0.807 g) as a solid which was used without additional purification.
Workup
- extractionextracted with ethyl acetate (×3)
- washThe combined organic extracts were washed with saturated aqueous sodium chloride
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e512293a40c643108b2ae12fe6075664
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08048907B2
Reaction notes
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