Diisopropyl Ether → HCID 13920705, compound

HRID 1284586Notes

Reaction equation

HRID 1284586 reaction equation
CC(OCC1C[S:14][C@@H:9]2[C@H:10](N)[C:11](=O)[N:8]2[C:7]=1[C:16](O)=O)=O.[S-]C#N.[K+].FC(F)(F)S(O)(=O)=O.[NH2:31][CH:32]1[C:46](=[O:47])[N:34]2[C:35]([C:43]([OH:45])=[O:44])=[C:36]([CH2:39]SC#N)[CH2:37][S:38][C@H:33]12.C(OC(C)C)(C)C>C(#N)C.C(O)(C)C.O.N1C=CC=CC=1>[S-:14][C:9]#[N:8].[NH2:31][CH:32]1[C:46](=[O:47])[N:34]2[C:35]([C:43]([OH:45])=[O:44])=[C:36]([CH2:39][N+:8]3[CH:7]=[CH:16][CH:9]=[CH:10][CH:11]=3)[CH2:37][S:38][C@H:33]12

Participants

10

Reactant 5

HCID 7914Diisopropyl EtherHCID 62406Trifluoromethanesulfonic acidHCID 4413287-Aminocephalosporanic acidHCID 516872Potassium thiocyanateHCID 88474068HCID 88474068, compound

Product 1

HCID 13920705HCID 13920705, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 7-aminocephalosporanic acid (45.0 g) and potassium thiocyanate (14.55 g) in acetonitrile (225 ml) was added dropwise trifluoromethanesulfonic acid (67.5 g) below 18° C. under cooling in an ice-bath and stirring, which was continued for 30 minutes at 15° to 18° C. The reaction mixture containing 7-amino-3-cyanothiomethyl-3-cephem-4-carboxylic acid was added to a mixture of pyridine (118.5 g) and water (150 ml) at 30° to 33.5° C. under stirring. The resultant mixture was immediately poured into a cold mixture of isopropyl alcohol (900 ml) and diisopropyl ether (1.2 l) under cooling in an ice-bath and stirring. The resulting precipitate was filtered, washed with isopropyl alcohol and diisopropyl ether and then redissolved in water (1.0 l). An insoluble material was filtered off and the filtrate was passed through a column packed with acidic alumina (150 g). The eluate (1.38 l) was concentrated to about 60 g of weight under reduced pressure and stirred for 30 minutes under cooling in an ice-bath. The resulting precipitate was filtered, washed with methanol and diisopropyl ether and dried to give 7-amino-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate thiocyanate (12.56 g), mp. 175° to 180° C. (dec.).

Workup

  1. temperatureunder cooling in an ice-bath
  2. stirringunder stirring
  3. temperatureunder cooling in an ice-bath
  4. stirringstirring
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with isopropyl alcohol and diisopropyl ether
  7. dissolutionredissolved in water (1.0 l)
  8. filtrationAn insoluble material was filtered off
  9. concentrationThe eluate (1.38 l) was concentrated to about 60 g of weight under reduced pressure
  10. stirringstirred for 30 minutes
  11. temperatureunder cooling in an ice-bath
  12. filtrationThe resulting precipitate was filtered
  13. washwashed with methanol and diisopropyl ether
  14. customdried

Sources & evidence

ORD record
ord-1c912883e52d4116b3b44934c5fb1a6e
Source dataset
uspto-grants-1986_01
Patent number
US04563449

Reaction notes

Loading…