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Sodium Hydroxide → (3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-tert.-butoxycarbonyl-2-azetidinone

HRID 34282
ノート
印刷プレビュー

反応式

HRID 34282 の反応式
[OH-].[Na+].[CH2:3]([O:6][C:7](Cl)=[O:8])[CH:4]=[CH2:5].[CH3:10][O:11][C:12]1[CH:33]=[CH:32][C:15]([CH2:16][N:17]2[C@H:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:19]([C@H:28]([OH:30])[CH3:29])[C:18]2=[O:31])=[CH:14][CH:13]=1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[C@H:20]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C@@H:19]([C@H:28]([O:30][C:7]([O:6][CH2:3][CH:4]=[CH2:5])=[O:8])[CH3:29])[C:18]2=[O:31])=[CH:32][CH:33]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformate2 回HCID 18604778(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone

生成物 1

HCID 18604780(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-tert.-butoxycarbonyl-2-azetidinone

試薬・触媒・溶媒 2

HCID 94433
Tetrabutylammonium hydrogen sulfate
触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

At 0°, 24 ml of 1N NaOH, 820 mg of tetrabutylammonium bisulphate and 1 ml of chloroformic acid allyl ester are added to a solution of 2 g of (3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone in 24 ml of methylene chloride and the whole is stirred vigorously. After a reaction time of 20 and 40 minutes, further portions (each of 1 ml) of chloroformic acid allyl ester are added. The reaction mixture is diluted with methylene chloride, the aqueous phase is separated off and the organic layer is washed in succession with 5% aqueous citric acid and 8% aqueous NaHCO3 solution and then dried and concentrated by evaporation. After purifying by chromatography, the pure, amorphous title compound is obtained.

後処理

  1. customthe aqueous phase is separated off
  2. washthe organic layer is washed in succession with 5% aqueous citric acid and 8% aqueous NaHCO3 solution
  3. customdried
  4. concentrationconcentrated by evaporation
  5. customAfter purifying by chromatography

出典と根拠

ORDレコード
ord-16963ddea0f6455db41136801f58d750
出典データセット
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04761408

反応ノート

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