Methanol → 7-Amino-3-vinyl-3-cephem-4-carboxylate hydrochloride

HRID 1195502Notes

Reaction equation

HRID 1195502 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].N1C=CC=CC=1.C(NC(C(OC(C1C=CC=CC=1)C1C=CC=CC=1)=O)CCCC([NH:28][CH:29]1[C:54](=[O:55])[N:31]2[C:32]([C:38]([O:40]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:39])=[C:33]([CH:36]=[CH2:37])[CH2:34][S:35][C@H:30]12)=O)(=O)C1C=CC=CC=1.CO>C(Cl)Cl.O.C(OCC)(=O)C>[ClH:2].[NH2:28][CH:29]1[C:54](=[O:55])[N:31]2[C:32]([C:38]([OH:40])=[O:39])=[C:33]([CH:36]=[CH2:37])[CH2:34][S:35][C@H:30]12

Participants

8

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 131713163Benzhydryl 7-(5-benzamido-5-benzhydryloxycarbonylpentanamido)-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 678600617-Amino-3-vinyl-3-cephem-4-carboxylate hydrochlorideYield 128.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of phosphorus pentachloride (15.5 g) in methylene chloride (200 ml) was added dropwise pyridine (5.9 g) at 5° to 10° C. with stirring, and the stirring was continued at 5° C. for 20 minutes. Thereto was added at a time benzhydryl 7-(5-benzamido-5-benzhydryloxycarbonylpentanamido)-3-vinyl-3-cephem-4-carboxylate (20 g) at 5° C., and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added gradually methanol (120 ml) at -40° C., followed by stirring at -20° to -10° C. for an hour. Removal of the solvent gave a residue, to which ethyl acetate (300 ml) and water (50 ml) were added. The mixture was stirred under ice-cooling for a while, and the precipitated crystals were collected by filtration and then washed with isopropyl alcohol to obtain benzydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride (8.4 g), mp 180°-195° C. (dec.).

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hours
  2. stirringby stirring at -20° to -10° C. for an hour
  3. customRemoval of the solvent
  4. customgave a residue
  5. stirringThe mixture was stirred under ice-
  6. temperaturecooling for a while
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-d29e457f4e5247279e4b7d6d9546e759
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

Loading…