Benzyl Bromide → HCID 131719734, compound

HRID 1079367Notes

Reaction equation

HRID 1079367 reaction equation
[C:1]([C:5]([C:7]1[N:12]2[C:13](=[S:17])[C@H:14]([O:15][CH3:16])[C@H:11]2[S:10](=[O:19])(=[O:18])[CH:9]([C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)[C:8]=1[CH3:26])=[O:6])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CS(C)=O.C(OCC)(=O)C>[CH2:34]([C:9]1([C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)[C:8]([CH3:26])=[C:7]([C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[O:6])[N:12]2[C:13](=[S:17])[C@H:14]([O:15][CH3:16])[C@H:11]2[S:10]1(=[O:19])=[O:18])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 131719733HCID 131719733, compound

Product 1

HCID 131719734HCID 131719734, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

415 mg of 4-tert-butylcarbonyl-7α-methoxy-3-methyl-2-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-3-cephem 1,1-dioxide was dissolved in dimethyl sulphoxide (3 ml) and triethylamine (0.153 ml) and benzyl bromide (0.360 ml) were added. The reaction mixture was left overnight at room temperature, diluted with ethyl acetate, washed with a dilute solution of hydrochloric acid and eventually with brine. Drying over Na2SO4 and removal of the organic solvent left a residue which was then purified by flash chromatography affording the title compound as a white solid (270 mg).

Workup

  1. washwashed with a dilute solution of hydrochloric acid and eventually with brine
  2. dry with materialDrying over Na2SO4 and removal of the organic solvent
  3. waitleft a residue which
  4. customwas then purified by flash chromatography

Sources & evidence

ORD record
ord-4c19d0c4c4074bcfbd9baa8fdc68d423
Source dataset
uspto-grants-1996_12
Patent number
US05580865

Reaction notes

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