Reaction equation
N[C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4].[BrH:10].N([O-])=O.[Na+]>O>[Br:10][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-2-aminohexanoic acid (FW 131.2, also known as L-norleucine) (1 g, 7.62 mmol), which is commercially available from Sigma Chemical Co at Sigmaaldrich.com, is dissolved in a mixture of HBr 48% (7.0 mL, 61 mmol) and H2O (10 mL). At 0° C., a solution of NaNO2 (1.7 g, 24 mmol) in H2O (5 mL) is added over a period of 30 min. The reaction is stirred for two hours. The reaction mixture is degassed in vacuo and extracted with EtOAc (2×20 mL). The extracts are washed with water (15 mL), dried (Na2SO4), filtered and evaporated to give (S)-2-bromohexanoic acid.
Workup
- customThe reaction mixture is degassed in vacuo
- extractionextracted with EtOAc (2×20 mL)
- washThe extracts are washed with water (15 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c80dfe6010ea41a0adda434b542efe92
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390789B2
Linked notes
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