Methyl iodide → HCID 88124709, compound

HRID 1079369Notes

Reaction equation

HRID 1079369 reaction equation
[CH:1]([O:14][C:15]1[C:16](=[O:43])[N:17]=[C:18]([S:22][CH:23]2[C:28]([CH3:29])=[C:27]([C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])[N:26]3[C:36](=[O:40])[C@H:37]([O:38][CH3:39])[C@H:25]3[S:24]2(=[O:42])=[O:41])[N:19]([CH3:21])[N:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[CH2:46](N(CC)CC)C>CS(C)=O.ClCCl>[CH:1]([O:14][C:15]1[C:16](=[O:43])[N:17]=[C:18]([S:22][C:23]2([CH3:46])[C:28]([CH3:29])=[C:27]([C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])[N:26]3[C:36](=[O:40])[C@H:37]([O:38][CH3:39])[C@H:25]3[S:24]2(=[O:41])=[O:42])[N:19]([CH3:21])[N:20]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 88125531HCID 88125531, compound

Product 1

HCID 88124709HCID 88124709, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(6-benzhydryloxy-2-methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)thio-4-tert-butylcarbonyl-7α-methoxy-3-methyl-3-cephem 1,1-dioxide (550 mg), prepared as described in PTC EP 90/02189 in dimethyl sulphoxide (4 ml) was treated with methyl iodide (0.170 ml) and triethylamine (0.147 ml). After 2 hrs the reaction was diluted with dichloromethane, washed in sequence with hydrochloric acid and brine, and dried Na2SO4. Removal of the solvent and flash chromatography of the crude residue gave the title compound (300 mg) as a yellowish solid.

Workup

  1. washwashed in sequence with hydrochloric acid and brine, and dried Na2SO4
  2. customRemoval of the solvent and flash chromatography of the crude residue

Sources & evidence

ORD record
ord-9f4ce95c219f4e9e852adb14c631483b
Source dataset
uspto-grants-1996_12
Patent number
US05580865

Reaction notes

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