반응 #62561

ord-a1ba749831c44b25a7dff0e80eb65fee

반응 방정식

O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+]
cerium(IV) ammonium nitrate
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N(Cc2ccc(OC)cc2)[C@@H]1OC(C)=O
(3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone
→
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N[C@@H]1OC(C)=O
(3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

반응물

O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+]
cerium(IV) ammonium nitrate
C=CCOC(=O)O[C@H](C)[C@H]1C(=O)N(Cc2ccc(OC)cc2)[C@@H]1OC(C)=O
(3R,4R)-1-(p-methoxybenzyl)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone

시약

없음

용매

O
water
CC#N
acetonitrile

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출After extraction with ethyl acetate
  2. 2
    세척washing with saturated NaHCO3 solution
  3. 3
    건조drying of the organic phase over sodium sulphate and concentration by evaporation under reduced pressure
  4. 4
    기타the crude title compound, which is purified by chromatography over silica gel
  5. 5
    기타is obtained

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04761408uspto-grants-1988_08