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

HRID 476300Notes

Reaction equation

HRID 476300 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([O-])=O.[Na+].[BrH:14]>O>[Br:14][C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 439524D-LeucineHCID 23668193Sodium Nitrite

Product 1

HCID 12697060(2R)-2-bromo-4-methylpentanoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

D-Leucine (9.9 g, 75.2 mmol) was dissolved in 3M HBr in water (120 mL) and cooled to 0° C. A solution of sodium nitrite (8.3 g, 120 mmol) in water (20 mL, 100 mmol) was added. The mixture was stirred at 0° C. for 2.5 hours, extracted twice with EtOAc, washed twice with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated to afford 12.6 g (86%) of Intermediate (9a) as a pale yellow oil. This was taken on to the next step without further purification.

Workup

  1. extractionextracted twice with EtOAc
  2. washwashed twice with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20547b53836d419996b16c6da7145684
Source dataset
uspto-grants-2014_01
Patent number
US08637676B2

Reaction notes

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