D-Leucine → (R)-2-hydroxy-4-methylpentanoic acid
Reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([O-])=[O:11].[Na+]>S(=O)(=O)(O)O.O>[OH:11][C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2.62 g of D-leucine in 30 ml of 1N sulfuric acid at 0° C. was added a solution of sodium nitrite (2.07 g) in water (15 ml). The resulting solution was stirred at 0° C. for 3 hours, and then at room temperature for 2 hours. The reaction mixture was extracted with ethyl ether (10 ml×3), and the combined organic layers were washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to yield the title compound as a light-yellow solid (2.08 g).
Workup
- waitat room temperature for 2 hours
- extractionThe reaction mixture was extracted with ethyl ether (10 ml×3)
- washthe combined organic layers were washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-44eba8cf94b94446a47ac484adafc57e
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380921
Reaction notes
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