Benzyl Bromide → HCID 178459028, compound

HRID 2255150Notes

Reaction equation

HRID 2255150 reaction equation
C(O[C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N+:7]([O-:16])[C:6]=1[NH2:17])C=C.[C:18](=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:32]([O:35][CH2:36][CH3:37])(=O)C>CN(C)C=O>[CH2:36]([O:35][CH2:32][C:5]1[C:6]([NH2:17])=[N+:7]([O-:16])[C:8]([CH2:12][CH:13]([CH3:14])[CH3:15])=[C:9]([O:11][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:10]=1)[CH:37]=[CH2:18]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178458957HCID 178458957, compound

Product 1

HCID 178459028HCID 178459028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 25 ml of dimethylformamide were dissolved 2.00 g of 6-allyloxy-5-amino-3-isobutyl-1,2-dihydropyrazin-2-one 4-oxide and 570 mg of potassium carbonate. Thereto was added 1.05 ml of benzyl bromide. The mixture was stirred for 1.5 hours at room temperature. After completion of the reaction, 200 ml of ethyl acetate was added to the reaction mixture. The resulting mixture was washed with water. The aqueous layer was extracted with 50 ml of ethyl acetate twice. The extract was combined with the above ethyl acetate layer. The combined mixture was washed with an aqueous solution saturated with NaCl, and dried with magnesium sulfate, then the solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (eluting solvent: 40% by volume of ethyl acetate-n-hexane), followed by recrystallization from n-hexane to obtain 1.57 g of 3-allyloxymethyl-2-amino-5-benzyloxy-6-isobutylpyrazine 1-oxide (Compound B-4) as white fine needle-like crystals having a melting point of 56.3°-57.2° C.

Workup

  1. additionwas added to the reaction mixture
  2. washThe resulting mixture was washed with water
  3. extractionThe aqueous layer was extracted with 50 ml of ethyl acetate twice
  4. washThe combined mixture was washed with an aqueous solution saturated with NaCl
  5. dry with materialdried with magnesium sulfate
  6. customthe solvent was removed by evaporation
  7. customThe residue was purified by a silica gel column chromatography (eluting solvent: 40% by volume of ethyl acetate-n-hexane)
  8. customfollowed by recrystallization from n-hexane

Sources & evidence

ORD record
ord-556bee671d7f494da990b150c997176f
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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