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Sodium hydride → benzyl 2-[(4R)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

HRID 232207
ノート
印刷プレビュー

反応式

HRID 232207 の反応式
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][NH:13][C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:20]1([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH:24]=[CH:23][C:22](=[O:25])[O:21]1>CN(C)C=O.C(OCC)(=O)C.O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][N:13]([C:20]3([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH:24]=[CH:23][C:22](=[O:25])[O:21]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 20030939HCID 20030939、化合物HCID 54136951HCID 54136951、化合物

生成物 1

HCID 67902028benzyl 2-[(4R)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate収率 20.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒
2 回
HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
-10 °C

実験手順

In 3 ml of anhydrous N,N-dimethylformamide was dissolved 220 mg of (4R)-4-phenylacetamido-3-isoxazolidinone. To the solution was added, under ice-cooling and stirring, 60 mg of sodium hydride (50% mineral oil), which was stirred for 10 minutes. Then the reaction solution was cooled to -10° C., to which was added under stirring 0.7 ml of anhydrous N,N-dimethylformamide solution dissolving 250 mg of the Compound (28) obtained in Example 28. The reaction solution was stirred at the same temperature for 45 minutes, followed by pouring into a mixture of ethyl acetate and water. The ethyl acetate layer was taken, washed with water and dried (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:1) to give 87 mg of the subject Compound (32) as colorless foamy substance.

後処理

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. additionwas added
  4. stirringThe reaction solution was stirred at the same temperature for 45 minutes
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated off
  8. washfollowed by elution with hexane-ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-3ecab5ff10a34380a1fc4a9d4812e11c
出典データセット
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04851422

反応ノート

読み込み中…

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