Methyl iodide → HCID 131719732, compound

HRID 1079366Notes

Reaction equation

HRID 1079366 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].[CH2:27](N(CC)CC)C.CI>CS(C)=O.C(OCC)(=O)C>[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])[C:9]([CH3:27])([C:20]2[N:24]([CH3:25])[N:23]=[N:22][N:21]=2)[C:8]=1[CH3:26])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 131719733HCID 131719733, compound

Product 1

HCID 131719732HCID 131719732, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-tert-butylcarbonyl-7α-methoxy-3-methyl-2-(1-methyl-1,2,3,4-tetrazol-5-yl)thio-3-cephem 1,1-dioxide (300 mg), prepared as described in PCT EP 90/02189 in dimethyl sulphoxide (3 ml), was treated at room temperature with triethylamine (0.110 ml) and methyl iodide (0.135 ml). After 1 hr, the reaction mixture was diluted with ethyl acetate, sequentially washed with a dilute solution of hydrochloric acid and brine and eventually dried over Na2SO4. Removal of the solvent and flash chromatography of the residue afforded the title compound as a white solid (160 mg).

Workup

  1. washsequentially washed with a dilute solution of hydrochloric acid and brine
  2. dry with materialeventually dried over Na2SO4
  3. customRemoval of the solvent and flash chromatography of the residue

Sources & evidence

ORD record
ord-2bd9316d06e046cd94da3c0b6f5e693d
Source dataset
uspto-grants-1996_12
Patent number
US05580865

Reaction notes

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