Water → HCID 86741232, compound

HRID 980486Notes

Reaction equation

HRID 980486 reaction equation
[Na].[S:2](=[C:5]([CH:13]([OH:16])[CH2:14][OH:15])[CH2:6][C:7]1[CH:12]=[N:11][CH:10]=[CH:9][N:8]=1)(=[O:4])=[O:3].[CH3:17]I.O>CO>[CH3:17][N:11]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:6][C:5](=[S:2](=[O:3])=[O:4])[CH:13]([OH:16])[CH2:14][OH:15])[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 86741233HCID 86741233, compound

Product 1

HCID 86741232HCID 86741232, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.2 g of 2-(2-sulfonyl-3,4-dihydroxybutyl) pyrazine sodium salt (4106 and 4107) was added to a solution of 10 ml of methyl iodide in 25 ml of methanol. 2 ml of water were added and the mixture was refluxed for 5 days. It was then concentrated, taken up in 100 ml of water and washed with methylene chloride. The aqueous layer was concentrated and the residue chromatographed (Biogel P-2/water) giving 1.1 g of 1-methyl-3-(2-sulfonyl-3,4-dihydroxybutyl)pyrazine (4100) as a mixture of diastereoisomers. UV H2O max: 283 (3.88). These were separated using a Biorad AG-50 W×4 (Ca++) column at 65° with water as the eluent. 13C NMR: 163.89, S (C3); 150.36, D (C5); 138.88, D, 135.81, D (C2, C6); 71.05, D (CHOH); 64.41, T (CH2OH); 61.64, D (CHSO3-); 49.65, Q (NCH3); 32.61, T (--CH2 --). 13C NMR of the epimer; 163.49, S (C3); 150.44, D (C5); 138.77, D, 135.92, D (C2, C6); 71.82, D (CHOH); 63.37, T (CH2OH); 63.25, D (CHSO3-); 49.65, Q (NCH3); 33.26, T (-CH2 -).

Workup

  1. temperaturethe mixture was refluxed for 5 days
  2. concentrationIt was then concentrated
  3. washwashed with methylene chloride
  4. concentrationThe aqueous layer was concentrated
  5. customthe residue chromatographed (Biogel P-2/water)

Sources & evidence

ORD record
ord-f35e8661ba604c7681559cc55c8a9598
Source dataset
uspto-grants-1987_01
Patent number
US04638005

Reaction notes

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