Dimethyl Sulfide → HCID 131711481, compound

HRID 26569Notes

Reaction equation

HRID 26569 reaction equation
[OH:1][CH:2]([CH:4]1[C:28](=[O:29])[N:6]2[CH:7]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:8](=C)[CH2:9][S:10][C@H:5]12)[CH3:3].C(Cl)Cl.[O:33]=[O+][O-].CSC>O=O>[OH:1][CH:2]([CH:4]1[C:28](=[O:29])[N:6]2[C:7]([C:12]([O:14][CH:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])=[C:8]([OH:33])[CH2:9][S:10][C@H:5]12)[CH3:3]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 24823OzoneHCID 131711482HCID 131711482, compound

Product 1

HCID 131711481HCID 131711481, compound

Reagents, catalysts & solvents 1

HCID 977OxygenSolvent

Procedure

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.

Workup

  1. additionAfter 1 minute at -78° the reaction mixture is treated with 5 ml
  2. waitfollowed by 1 hour at 25° C
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-30a8d11a21f34e4da5c116ae9c48021a
Source dataset
uspto-grants-1979_04
Patent number
US04150156

Reaction notes

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