Potassium Bromide → HCID 53916216, compound
Reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][CH2:12][C@@H:13](N)[C:14]([OH:16])=[O:15])=[O:10])=[CH:3][CH:2]=1.[K+].[Br-:19].N([O-])=O.[Na+]>OS(O)(=O)=O>[Br:19][C@H:13]([CH2:12][CH2:11][C:9]([O:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:10])[C:14]([OH:16])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of D-glutamic acid γ-benzyl ester (5.00 g, 21 mmol) and KBr (7.5 g, 63 mmol) in 2.5N H2SO4 (35 mL) at 0° C. (ice bath) was added NaNO2 (2.45 g, 35.5 mmol) in small portions over 1.5 hrs keeping the internal temperature below 5° C. The resulting mixture was stirred at 0° C. for 1 hr and at room temperature for 45 min. The mixture was extracted with Et2O, extract washed with water and saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was taken up in CH2Cl2, re-dried over Na2SO4 and evaporated to dryness to give crude (2R)-2-bromo-4-carbobenzyloxy-butyric acid (5.52 g) as a colorless oil.
Workup
- customthe internal temperature below 5° C
- extractionThe mixture was extracted with Et2O
- extractionextract
- washwashed with water and saturated NaCl solution
- dry with materialdried over anhydrous Na2SO4
- customevaporated to dryness
- dry with materialre-dried over Na2SO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-333e7770e9b3453c988cdb29fcb65840
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06242422B1
Reaction notes
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