Sodium Hydroxide → (2R,3R)-2,3-epoxybutyric acid p-methoxybenzylamide

HRID 34280Notes

Reaction equation

HRID 34280 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][NH:10][C:11](=[O:17])[C@@H:12](Br)[C@H:13]([OH:15])[CH3:14])=[CH:7][CH:6]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][NH:10][C:11](=[O:17])[C@@H:12]2[O:15][C@@H:13]2[CH3:14])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 56611729HCID 56611729, compound

Product 1

HCID 13488847(2R,3R)-2,3-epoxybutyric acid p-methoxybenzylamide

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

50 ml of 50% NaOH solution and 456 mg (2 mmol) of benzyltriethylammonium chloride are added to a solution of 6.04 g (20 mmol) of (2S,3R)-2-bromo-3-hydroxybutyric acid p-methoxybenzylamide in 150 ml of methylene chloride. The two-phase mixture is stirred vigorously for 20 hours at room temperature. The organic layer is separated off and the aqueous phase is then extracted with methylene chloride. The combined methylene chloride solutions are dried and concentrated by evaporation. The resulting crude product is chromatographed over 40 times its weight of silica gel in the system methylene chloride/methanol (99:1). After crystallisation of the pure fractions from methylene chloride/diethyl ether/petroleum ether, the title compound, melting point 75°-76°, is obtained.

Workup

  1. customThe organic layer is separated off
  2. extractionthe aqueous phase is then extracted with methylene chloride
  3. dry with materialThe combined methylene chloride solutions are dried
  4. concentrationconcentrated by evaporation
  5. customThe resulting crude product is chromatographed over 40 times its weight of silica gel in the system methylene chloride/methanol (99:1)
  6. customAfter crystallisation of the pure fractions from methylene chloride/diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-9873c437cb8e4c9c9afb2e970af164f3
Source dataset
uspto-grants-1988_08
Patent number
US04761408

Reaction notes

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