Diketene → HCID 131714995, compound

HRID 1249419Notes

Reaction equation

HRID 1249419 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7]Br.[NH2:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:14](/[CH:17]=[CH:18]/[Cl:19])[CH2:15][S:16][C@H:11]12.C[Si](CC(N)=O)(C)C>C(Cl)Cl.C(OCC)(=O)C.O>[Br:7][CH2:6][C:2](=[O:1])[CH2:3][C:4]([NH:9][CH:10]1[C:36](=[O:37])[N:12]2[C:13]([C:20]([O:22][CH:23]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:14](/[CH:17]=[CH:18]/[Cl:19])[CH2:15][S:16][C@H:11]12)=[O:5]

Participants

8

Reactant 4

HCID 12661DiketeneHCID 24408BromineHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 88686710HCID 88686710, compound

Product 1

HCID 131714995HCID 131714995, compoundYield 101.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diketene (1.01 g) in methylene chloride (15 ml) was dropwise added bromine (1.53 g) at -20° C., and the mixture was stirred at the same temperature for 20 minutes and added to a solution of benzhydryl 7-amino-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (3.42 g) and trimethylsilylacetamide (5.3 g) in ethyl acetate (40 ml) at the same temperature. The reaction mixture was stirred at -10° to -15° C. for 10 minutes, poured into water and extracted with ethyl acetate. The extract was washed with 10% aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was triturated with diisopropyl ether and collected by filtration to give benzhydryl 7-(4-bromo-3-oxobutyramido)-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (4.8 g).

Workup

  1. customat -20° C.
  2. stirringThe reaction mixture was stirred at -10° to -15° C. for 10 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with 10% aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was triturated with diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4740f79cb19e4a159e55a2f750e57f54
Source dataset
uspto-grants-1986_12
Patent number
US04631274

Reaction notes

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