Acetonitrile → benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

HRID 2351141Notes

Reaction equation

HRID 2351141 reaction equation
[NH2:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:6](OS(C)(=O)=O)[CH2:7][S:8][C@H:3]12.C[Si](N[C:37]([NH:39][Si](C)(C)C)=O)(C)C.[C:44](#N)[CH3:45]>>[NH2:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:15])=[C:6]([S:8]/[CH:7]=[CH:6]\[C:5]3[CH:14]=[N:39][CH:37]=[CH:45][CH:44]=3)[CH2:7][S:8][C@H:3]12

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 875621,3-Bis(trimethylsilyl)ureaHCID 88528619Benzhydryl 7-amino-3-mesyloxy-3cephem-4-carboxylate

Product 1

HCID 67948113benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

Procedure

The mixture was stirred for 30 minutes. To the mixture was added a solution of benzhydryl 7-amino-3-mesyloxy-3-cephem-4-carboxylate (9.21 g) and bis-(trimethylsilyl)urea (12.26 g) in acetonitrile (276 ml) under ice-cooling. The reaction mixture was stirred for 10 minutes at the same temperature. The insoluble material was filtered off. The filtrate was concentrated in vacuo and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (6.17 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 10 minutes at the same temperature
  3. filtrationThe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe ethyl acetate solution was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-28f01401d39e466cb67a7457e858887a
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

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