Sulfuric Acid → HCID 54211560, compound

HRID 397309Notes

Reaction equation

HRID 397309 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].S(=O)(=O)(O)O.[CH3:16][C:17](=[CH2:19])[CH3:18].[OH-].[Na+]>C(OCC)(=O)C.O1CCOCC1>[C:17]([O:7][C:6](=[O:8])[C@H:4]([CH2:3][C:2]([CH3:10])([CH3:9])[CH3:1])[NH2:5])([CH3:19])([CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 14798Sodium Hydroxide2×HCID 194032(2S)-2-Amino-4,4-dimethylpentanoic acid

Product 1

HCID 54211560HCID 54211560, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a pressure bottle were added 1.5 gm (10.3 mMol) 4-methyl-(L)-leucine, 25 mL dioxane, 1.5 mL concentrated sulfuric acid and 25 mL isobutylene. The pressure bottle was stoppered and the reactants were shaken together for 18 hours. The reaction mixture was then treated with 60 mL cold 1N sodium hydroxide and 100 mL ethyl acetate. To this mixture was added sufficient 1N sodium hydroxide until the pH of the mixture was 8.5. The layers were separated and the aqueous phase was extracted well with ethyl acetate. The combined ethyl acetate phases were dried over sodium sulfate and concentrated under reduced pressure to provide an oil which gradually crystallized to provide 1.05 gm (50.5%) of the title compound.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted well with ethyl acetate
  3. dry with materialThe combined ethyl acetate phases were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide an oil which
  6. customgradually crystallized

Sources & evidence

ORD record
ord-5d9c1bd03b5242cc91317327f5a3abcb
Source dataset
uspto-grants-2003_08
Patent number
US06610680B1

Reaction notes

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