Dichloromethane → HCID 15065178, compound

HRID 2255159Notes

Reaction equation

HRID 2255159 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH2:6]([O:13][C:14]1[C:15]([CH2:25][CH:26]([CH3:28])[CH3:27])=[N+:16]([O-:24])[C:17]([O:22][CH3:23])=[C:18]([CH2:20][OH:21])[N:19]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.ClCCl.C(N(CC)CC)C>C(OCC)C>[CH2:6]([O:13][C:14]1[C:15]([CH2:25][CH:26]([CH3:28])[CH3:27])=[N+:16]([O-:24])[C:17]([O:22][CH3:23])=[C:18]([CH2:20][O:21][S:1]([CH3:4])(=[O:3])=[O:2])[N:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 9818439HCID 9818439, compound

Product 1

HCID 15065178HCID 15065178, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At 0° C., 52 μl of mesyl chloride was added to a mixture of 210 mg of 3-benzyloxy-5-hydroxymethyl-6-methoxy-2-isobutylpyrazine 1-oxide, 2 ml of dichloromethane and 184 μl of triethylamine. The mixture was stirred for 30 minutes at the same temperature, then diethyl ether was added to the reaction mixture. The mixture was washed with water and dried over magnesium sulfate, then the solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (eluting solvent: 50% by volume of ethyl acetate-n-hexane) to obtain 260 mg of 3-benzyloxy-2-isobutyl-6-methoxy-5-mesyloxymethylpyrazine 1-oxide (Compound B-17) as a colorless oily substance.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was removed by evaporation
  4. customThe residue was purified by a silica gel column chromatography (eluting solvent: 50% by volume of ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-3eb9f57dc8454c30905f7749b5f31578
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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