Methanol → HCID 9818439, compound

HRID 2255158Notes

Reaction equation

HRID 2255158 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:26][CH:27]([CH3:29])[CH3:28])=[N+:11]([O-:25])[C:12]([O:23][CH3:24])=[C:13]([CH2:15][O:16]C2CCCCO2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>Cl.C(OCC)C>[CH2:1]([O:8][C:9]1[C:10]([CH2:26][CH:27]([CH3:29])[CH3:28])=[N+:11]([O-:25])[C:12]([O:23][CH3:24])=[C:13]([CH2:15][OH:16])[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 15065177HCID 15065177, compound

Product 1

HCID 9818439HCID 9818439, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

There was stirred, for 30 minutes at room temperature, a mixture of 80 mg of 3-benzyloxy-2-isobutyl-6-methoxy-5-(2-tetrahydropyranyloxymethyl)pyrazine 1-oxide, 1 ml of methanol and one drop of concentrated hydrochloric acid. The reaction mixture was mixed with diethyl ether, then the mixture was washed with an aqueous solution saturated over sodium hydrogen carbonate, and dried over magnesium sulfate. The solvent was removed by evaporation. The residue was purified by a silica gel thin layer chromatography (developing solvent: 50% by volume of ethyl acetate-n-hexane), followed by recrystallization from diethyl ether-n-hexane to obtain 63 mg of 3-benzyloxy-5-hydroxymethyl-2-isobutyl-6-methoxypyrazine 1-oxide (Compound B-16) as colorless needle-like crystals having a melting point of 68.0°-69.2° C.

Workup

  1. washthe mixture was washed with an aqueous solution saturated over sodium hydrogen carbonate
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed by evaporation
  4. customThe residue was purified by a silica gel thin layer chromatography (developing solvent: 50% by volume of ethyl acetate-n-hexane)
  5. customfollowed by recrystallization from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-175ee013863e4c89a6644da83d4f7c4e
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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