Potassium Carbonate → Benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate

HRID 704261Notes

Reaction equation

HRID 704261 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH:12]([NH:14][CH:15]1[C:39](=[O:40])[N:17]2[C:18]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:19]([OH:22])[CH2:20][S:21][C@H:16]12)=[O:13]>CN(C)C=O>[CH:12]([NH:14][CH:15]1[C:39](=[O:40])[N:17]2[C:18]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:24])=[C:19]([O:22][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:20][S:21][C@H:16]12)=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2×HCID 88528581Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

Product 1

HCID 88528775Benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-30 °C

Procedure

Mesyl chloride (0.66 ml) and potassium carbonate (1.38 g) were added to a solution of benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate (2.05 g) in N,N-dimethylformamide (6 ml) at -30° C. The mixture was stirred at -30° C. for 30 minutes. Mesyl chloride (0.4 ml) was added to the mixture. The reaction mixture was stirred at -30° C. for 20 minutes, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and filtered, and the filtrate was evaporated in vacuo. The residue was dissolved in a small amount of ethyl acetate and the mixture was subjected to column chromatography on silica gel and eluted with a mixture of benzene and ethyl acetate (1:1). The eluent was evaporated in vacuo. The residue was triturated with diisopropyl ether to give benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate (0.85 g).

Workup

  1. stirringThe reaction mixture was stirred at -30° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  8. washeluted with a mixture of benzene and ethyl acetate (1:1)
  9. customThe eluent was evaporated in vacuo
  10. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-0da1846da2e04d90ae4f05bb7803ae7f
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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