Dimethyl Sulfide → HCID 131714493, compound

HRID 1284585Notes

Reaction equation

HRID 1284585 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[CH3:19][S:20][CH3:21].[F:22][C:23]([F:29])([F:28])[S:24]([OH:27])(=[O:26])=[O:25].C(OCC)(=O)C>C(#N)C>[F:22][C:23]([F:29])([F:28])[S:24]([O-:27])(=[O:26])=[O:25].[F:22][C:23]([F:29])([F:28])[S:24]([OH:27])(=[O:26])=[O:25].[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S+:20]([CH3:21])[CH3:19])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8857Ethyl AcetateHCID 62406Trifluoromethanesulfonic acidHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 131714493HCID 131714493, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7-aminocephalosporanic acid (6.0 g) and dimethyl sulfide (1.36 g) in acetonitrile (30 ml) was added trifluoromethanesulfonic acid (9.0 g) below 18° C. under cooling in an ice-bath and stirring, which was continued for 30 minutes at 15° to 18° C. To the reaction mixture was added ethyl acetate (80 ml), and the mixture was seeded and stirred for one hour at ambient temperature. A resulting precipitate was filtered, washed with ethyl acetate and dried to give 7-amino-3-dimethylsulfoniomethyl-3-cephem-4-carboxylate bis(trifluoromethanesulfonate) (8.55 g), mp. 190° to 195° C. (dec.).

Workup

  1. temperatureunder cooling in an ice-bath
  2. stirringstirred for one hour at ambient temperature
  3. filtrationA resulting precipitate was filtered
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-b0cf809e25d64f698169574590aa2276
Source dataset
uspto-grants-1986_01
Patent number
US04563449

Reaction notes

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