3-Hydroxybutyrolactone, (3S)- → (3S)-3-acetyloxy-4-bromobutanoic acid

HRID 1595029

Reaction equation

HRID 1595029 reaction equation
[OH:1][C@@H:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.[BrH:8].[C:9]([OH:12])(=O)[CH3:10]>C(Cl)Cl>[C:9]([O:1][C@H:2]([CH2:7][Br:8])[CH2:3][C:4]([OH:6])=[O:5])(=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 72693893-Hydroxybutyrolactone, (3S)-HCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 2733880(3S)-3-acetyloxy-4-bromobutanoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-3-hydroxybutyrolactone (10 g) in 85% purity and hydrogen bromide/acetic acid (40 ml) in 30% purity was charged to a 250 ml flask equipped with a thermometer, reflux condensor and agitator, and stirred at 40˜60° C. for 5 hours. After the reaction was completed, the reaction solution was cooled at room temperature. With the addition of methylene chloride (200 ml), the mixture washed with 1M sodium acetate solution and then an organic layer was separated, dried over anhydrous magnesium sulfate, filtered off and concentrated. Toluene (100 ml) was added to (S)-3-acetoxy-4-bromobutyric acid, so concentrated, to remove the remaining acetic acid. The concentration under reduced pressure gave 18.74 g of (S)-3-acetoxy-4-bromobutyric acid (yield: 85%).

Workup

  1. customequipped with a thermometer
  2. temperaturereflux condensor and agitator
  3. washthe mixture washed with 1M sodium acetate solution
  4. customan organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. additionToluene (100 ml) was added to (S)-3-acetoxy-4-bromobutyric acid
  9. concentrationso concentrated
  10. customto remove the remaining acetic acid
  11. concentrationThe concentration under reduced pressure

Sources & evidence

ORD record
ord-94ed71b06d154bec8e4a27635cdd4997
Source dataset
uspto-grants-2001_09
Patent number
US06284902B1

Linked notes

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