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

HRID 232207
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HRID 232207 반응식
[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
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참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 20030939HCID 20030939, 화합물HCID 54136951HCID 54136951, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매
HCID 6228
Dimethylformamide
용매
2회
HCID 8857Ethyl Acetate용매2회

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온도
-10 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ecab5ff10a34380a1fc4a9d4812e11c
출처 데이터셋
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04851422

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