Hydrochloric Acid → (2S,3S)-2-Chloro-3-methylvaleric Acid

HRID 1074106Notes

Reaction equation

HRID 1074106 reaction equation
N[C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[ClH:10].N([O-])=O.[Na+]>CCOCC>[Cl:10][C@@H:2]([C@@H:3]([CH3:4])[CH2:5][CH3:6])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6306L-IsoleucineHCID 23668193Sodium Nitrite

Product 1

HCID 11051847(2S,3S)-2-Chloro-3-methylvaleric Acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

L-isoleucine (105 g) was added to 6N-hydrochloric acid (1 l), followed by agitating the mixture, cooling it with ice, adding sodium nitrite (80 g), agitating the mixture at 0° C. for 3 hours, adding ether (300 ml), separating the resulting organic layer, extracting the aqueous layer with ether (150 ml), combining the organic layers, drying over MgSO4, distilling off ether and distilling the residue under reduced pressure, to obtain (2S,3S)-2-chloro-3-methylvaleric acid (34.2 g, b.p. 96-97/4 mmHg).

Workup

  1. temperaturecooling it with ice
  2. stirringagitating the mixture at 0° C. for 3 hours
  3. customseparating the resulting organic layer
  4. extractionextracting the aqueous layer with ether (150 ml)
  5. dry with materialdrying over MgSO4
  6. distillationdistilling off ether
  7. distillationdistilling the residue under reduced pressure

Sources & evidence

ORD record
ord-de4d2c1897694cdea7cdb0983574c0c4
Source dataset
uspto-grants-1990_11
Patent number
US04973426

Reaction notes

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