Norleucine, D-(-)- → Hexanoic acid, 2-hydroxy-, (2R)-
Reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].N([O-])=[O:11].[Na+]>S(=O)(=O)(O)O.O>[OH:11][C@H:2]([CH2:3][CH2:4][CH2:5][CH3:6])[C:7]([OH:9])=[O:8]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.), stirred solution of D-norleucine (500 mg, 3.81 mmol) in 10 mL of 1N aqueous sulfuric acid was added sodium nitrite (421 mg, 6.10 mmol) in 3 mL of water dropwise over a 20-minute period. The reaction mixture was allowed to slowly warm to room temperature over a 16-hour period. The mixture then was extracted with EtOAc (2×25 mL), dried (Na2SO4), and concentrated to yield 200 mg (40%) of a white waxy solid.
Workup
- temperatureto slowly warm to room temperature over a 16-hour period
- extractionThe mixture then was extracted with EtOAc (2×25 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customto yield 200 mg (40%) of a white waxy solid
Sources & evidence
- ORD record
- ord-179b506ce4f74a2ca29ba9e4692847d9
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06998416B2
Reaction notes
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