Hydrogen Bromide → (2R)-2-bromo-4-methylpentanoic acid

HRID 475665Notes

Reaction equation

HRID 475665 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[BrH:10].O.N([O-])=O.[Na+]>>[Br:10][C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 962Water2×HCID 439524D-LeucineHCID 23668193Sodium Nitrite

Product 1

HCID 12697060(2R)-2-bromo-4-methylpentanoic acid

Conditions

Temperature
0 °C

Procedure

D-leucine (23.3 g, 177.3 mmol, 1.0 eq) was dissolved into 3.0M HBr in water (280 mL, 840 mmol) and cooled to 0° C. A solution of NaNO2 (19.6 g, 284 mmol) in water (31.9 mL, 1.8 mol) was slowly added over 20 minutes and the mixture was stirred at 0° C. for 3 hours. The mixture was extracted with ethyl ether (2×500 mL), washed with water (100 mL) and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated, to yield (R)-2-bromo-4-methylpentanoic acid as an off-yellow yellow oil (33.4 g).

Workup

  1. extractionThe mixture was extracted with ethyl ether (2×500 mL)
  2. washwashed with water (100 mL) and saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e6c2615bd2c14ee0a4539cb17eb9f840
Source dataset
uspto-grants-2014_01
Patent number
US08637562B2

Reaction notes

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