Water → HCID 88474068, compound

HRID 622762Notes

Reaction equation

HRID 622762 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.[S-:19][C:20]#[N:21].[K+].FC(F)(F)S(O)(=O)=O.O>C(#N)C>[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:19][C:20]#[N:21])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 4

HCID 962WaterHCID 62406Trifluoromethanesulfonic acidHCID 4413287-Aminocephalosporanic acidHCID 516872Potassium thiocyanate

Product 1

HCID 88474068HCID 88474068, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7-aminocephalosporanic acid (40 g) and potassium thiocyanate (15.7 g) in acetonitrile (200 ml) was added dropwise trifluoromethanesulfonic acid (40 ml) below 15° C. under cooling in an ice-bath and stirring, which was continued for 30 minutes at 5° to 15° C. and for 40 minutes at ambient temperature. The reaction mixture was poured into cold water (400 ml) and stirred for 30 minutes. The resulting precipitate was filtered, washed with water and acetone and dried to give 7-amino-3-cyanothiomethyl-3-cephem-4-carboxylic acid (26.2 g), mp. 175° to 180° C. (dec.).

Workup

  1. temperatureunder cooling in an ice-bath
  2. stirringstirred for 30 minutes
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and acetone
  5. customdried

Sources & evidence

ORD record
ord-0c54d3b2801b4d0abdf85013ec14aca3
Source dataset
uspto-grants-1988_09
Patent number
US04772682

Reaction notes

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