Sodium Chloride → (2R,3S)-2-hydroxy-3-methylpentanoic acid

HRID 1274808Notes

Reaction equation

HRID 1274808 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].N([O-])=[O:11].[Na+].C([O-])(O)=O.[Na+].[Na+].[Cl-]>OS(O)(=O)=O.O>[OH:11][C@H:2]([C@@H:3]([CH3:4])[CH2:5][CH3:6])[C:7]([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 94206D-AlloisoleucineHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 10820562(2R,3S)-2-hydroxy-3-methylpentanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of (-)-D-allo-isoleucine [1.00 g, 7.634 mmol, [α]D20 =-37°(5% in 6M HCl)] in 26 ml of 1N aq. H2SO4 at 2° was slowly added (ca. 12 h) a solution of NaNO2 (1.67 g, 24.13 mmol) in 26 ml of demineralised water. After stirring overnight at room temperature, 0.62 g of powdered NaHCO3 were added to bring the pH above 2. The solution was saturated with NaCl and extracted 6 times with ethyl acetate, maintaining the pH between 2 and 3 (1N aq. H2SO4, pH meter). After drying (Na2SO4), the organic layer was concentrated and the crude product (0.91 g, 91%) was directly used in the next step without further purification.

Workup

  1. extractionextracted 6 times with ethyl acetate
  2. temperaturemaintaining the pH between 2 and 3 (1N aq. H2SO4, pH meter)
  3. dry with materialAfter drying (Na2SO4)
  4. concentrationthe organic layer was concentrated
  5. customthe crude product (0.91 g, 91%) was directly used in the next step without further purification

Sources & evidence

ORD record
ord-2fe294be15044490aa04de0b79c161b9
Source dataset
uspto-grants-2000_12
Patent number
US06159929

Reaction notes

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