L-Leucine → (S)-4-isopropyloxazolidine-2,5-dione
Reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl[C:11](Cl)([O:13]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH3:5][CH:4]([CH2:3][CH:2]1[NH:1][C:11](=[O:13])[O:9][C:7]1=[O:8])[CH3:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
L-Leucine (15.00 g, 0.1144 mol) was heated to 100° C. under vacuum overnight, suspended in THF (150 ml) and stirred at 45° C. in a 3-neck flask with a reflux condenser fitted, under N2 pressure. Triphosgene (13.574 g, 0.4 eq) was added via a solid addition tube. After ca 80 min, the reaction had gone clear and the mixture was washed with dry diethyl ether (1 L) through the filter agent Celite (5 cm deep) in a sinter funnel (diameter 8 cm porosity 3) to a RB flask.
Workup
- customfitted, under N2 pressure
- waitAfter ca 80 min
- washthe mixture was washed with dry diethyl ether (1 L) through the filter agent Celite (5 cm deep) in a sinter funnel (diameter 8 cm porosity 3) to a RB flask
Sources & evidence
- ORD record
- ord-a2e22798bc27436f9dfbbd1951d8be33
- Source dataset
- uspto-grants-2005_01
- Patent number
- US06841689B2
Reaction notes
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