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

HRID 34281ノート

反応式

HRID 34281 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0d5f1f60881142b2aa9bebc35da62fdb
出典データセット
uspto-grants-1988_08
特許番号
US04761408

反応ノート

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