Sodium hydride → (2R,3R)-2,3-epoxybutyric acid N-tert.-butoxycarbonylmethyl-N-p-methoxybenzylamide

HRID 34281Notes

Reaction equation

HRID 34281 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][NH:8][C:9](=[O:14])[C@@H:10]2[O:13][C@@H:11]2[CH3:12])=[CH:5][CH:4]=1.[H-].[Na+].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[C:19]([O:23][C:24]([CH2:25][N:8]([CH2:7][C:6]1[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:9](=[O:14])[C@@H:10]1[O:13][C@@H:11]1[CH3:12])=[O:27])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 13488847(2R,3R)-2,3-epoxybutyric acid p-methoxybenzylamide

Product 1

HCID 86742306(2R,3R)-2,3-epoxybutyric acid N-tert.-butoxycarbonylmethyl-N-p-methoxybenzylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.21 g of (2R,3R)-2,3-epoxybutyric acid p-methoxybenzylamide in 100 ml of THF is added dropwise to a mixture, stirred at 0° under an argon atmosphere, of 550 mg of sodium hydride dispersion (55-60% in oil) and 1.52 ml of bromoacetic acid tert.-butyl ester in 25 ml of THF. The reaction mixture is heated to room temperature and stirred for a further 1 hour (reaction monitored by thin-layer chromatography). Total reaction time: 90 minutes. The insoluble portions are filtered off and washed with THF and the combined filtrates are concentrated by evaporation. The resulting crude product is purified by chromatography over 150 g of silica gel (system: toluene, toluene/ethyl acetate 80:20). Concentration of the pure fractions by evaporation yields the amorphous title compound.

Workup

  1. custom(reaction monitored by thin-layer chromatography)
  2. custom90 minutes
  3. filtrationThe insoluble portions are filtered off
  4. washwashed with THF
  5. concentrationthe combined filtrates are concentrated by evaporation
  6. customThe resulting crude product is purified by chromatography over 150 g of silica gel (system: toluene, toluene/ethyl acetate 80:20)
  7. customConcentration of the pure fractions by evaporation

Sources & evidence

ORD record
ord-0d5f1f60881142b2aa9bebc35da62fdb
Source dataset
uspto-grants-1988_08
Patent number
US04761408

Reaction notes

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