반응 #54847

ord-30a8d11a21f34e4da5c116ae9c48021a

반응 방정식

CSC
dimethyl sulfide
O=[O+][O-]
ozone
C=C1CS[C@@H]2C(C(C)O)C(=O)N2C1C(=O)OC(c1ccccc1)c1ccccc1
Benzhydryl 7-(1-hydroxyethyl)-3-methylene-cepham-4-carboxylate
ClCCl
CH2Cl2
CC(O)C1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(O)CS[C@H]12
benzhydryl 7-(1-hydroxyethyl)-3-hydroxy-3-cephem-4carboxylate

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONAfter 1 minute at -78° the reaction mixture is treated with 5 ml
  2. 2
    workup.WAITfollowed by 1 hour at 25° C
  3. 3
    기타The solvent is removed under reduced pressure

실험 절차

Benzhydryl 7-(1-hydroxyethyl)-3-methylene-cepham-4-carboxylate (4.6 g.) is dissolved in 500 ml. of CH2Cl2, cooled to -78° and treated with a stream of ozone in oxygen until a blue color persists in the reaction mixture. After 1 minute at -78° the reaction mixture is treated with 5 ml. of dimethyl sulfide and the reaction mixture is allowed to stand at -78° for 20 min. followed by 1 hour at 25° C. The solvent is removed under reduced pressure to give the crude benzhydryl 7-(1-hydroxyethyl)-3-hydroxy-3-cephem-4carboxylate.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04150156uspto-grants-1979_04