Sodium Chloride → (R)-2-hydroxy-4-methylpentanoic acid

HRID 2079269Notes

Reaction equation

HRID 2079269 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([O-])=[O:11].[Na+].[Cl-].[Na+]>S(=O)(=O)(O)O.O>[OH:11][C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 439524D-LeucineHCID 23668193Sodium Nitrite

Product 1

HCID 439960(R)-2-hydroxy-4-methylpentanoic acidYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

To a cooled solution (0-5° C.) of D-leucine (200 g, 1.5 mol) in sulfuric acid (3 L, 1 M) was added dropwise a solution of sodium nitrite (240 g, 3.5 mol) in water (1 L) while maintaining the temperature between 0-5° C. The reaction mixture was stirred at room temperature overnight. The solution was saturated with sodium chloride and extracted with tert-butyl methyl ether (3×). The combined organic layers were dried over Na2SO4 and filtered, and the solvent was removed in vacuo. (R)-α-hydroxyisocaproic acid was isolated as a white solid in a yield of 67% (132 g).

Workup

  1. extractionextracted with tert-butyl methyl ether (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f0dd665a073843ccb6e22f2b8e7eeb35
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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