Ammonium cerium (IV) nitrate → (3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

HRID 34283

반응식

HRID 34283 반응식
[N+]([O-])([O-])=O.[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.COC1C=CC(C[N:30]2[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@@H:32]([C@H:38]([O:40][C:41]([O:43][CH2:44][CH:45]=[CH2:46])=[O:42])[CH3:39])[C:31]2=[O:47])=CC=1>O.C(#N)C>[CH2:44]([O:43][C:41]([O:40][C@@H:38]([C@@H:32]1[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[NH:30][C:31]1=[O:47])[CH3:39])=[O:42])[CH:45]=[CH2:46]

참가 물질

5

반응물 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 18604779(3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

생성물 1

HCID 18604782(3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

At 10°, a solution of 5.37 g of cerium(IV) ammonium nitrate in 15 ml of water is added to a solution of 900 mg (1.18 mmol) of (3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone in 30 ml of acetonitrile, and the whole is stirred for two hours at room temperature. After extraction with ethyl acetate, washing with saturated NaHCO3 solution, drying of the organic phase over sodium sulphate and concentration by evaporation under reduced pressure, the crude title compound, which is purified by chromatography over silica gel using toluene/ethyl acetate (4:1 and 1:1), is obtained.

후처리

  1. extractionAfter extraction with ethyl acetate
  2. washwashing with saturated NaHCO3 solution
  3. dry with materialdrying of the organic phase over sodium sulphate and concentration by evaporation under reduced pressure
  4. customthe crude title compound, which is purified by chromatography over silica gel
  5. customis obtained

출처 및 근거

ORD 기록
ord-a1ba749831c44b25a7dff0e80eb65fee
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761408

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