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

HRID 34282

반응식

HRID 34282 반응식
[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

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformate2회HCID 18604778(3S,4S)-1-(p-methoxybenzyl)-3-[(1R)-1-hydroxyethyl)-4-tert.-butoxycarbonyl-2-azetidinone

생성물 1

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

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-16963ddea0f6455db41136801f58d750
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761408

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