Hydrochloric Acid → HCID 178441366, compound

HRID 2255154Notes

Reaction equation

HRID 2255154 reaction equation
ClCCl.[NH2:4][C:5]1[C:10]([C:11](OCC)=[O:12])=[N:9][C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:7]([CH2:24][CH:25]([CH3:27])[CH3:26])[N+:6]=1[O-:28].[H-].C([Al+]CC(C)C)C(C)C.Cl>CCCCCC.O>[NH2:4][C:5]1[C:10]([CH2:11][OH:12])=[N:9][C:8]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:7]([CH2:24][CH:25]([CH3:26])[CH3:27])[N+:6]=1[O-:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 21225700DiisobutylaluminumhydrideHCID 178470316HCID 178470316, compound

Product 1

HCID 178441366HCID 178441366, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-35 °C

Procedure

14 Milliliters of dry dichloromethane was added to 670 mg of 2-amino-5-benzyloxy-3-ethoxycarbonyl-6-isobutylpyrazine 1-oxide. The mixture was cooled to -35° C. Thereto was dropwise added in about 5 minutes 4.7 ml of a solution of 1 mol of diisobutylaluminum hydride dissolved in n-hexane. After completion of the dropwise addition, a reaction was effected for 40 minutes at -30° C., then the temperature of the reaction mixture was returned to room temperature by adding 1 ml of water to the reaction mixture. Further, 30 ml of 2% hydrochloric acid was added thereto and the reaction mixture was extracted with dichloromethane, and the extract was dried over magnesium sulfate. The solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (eluting solvent: 70% by volume of methanol-dichloromethane), followed by recrystallization from benzene to obtain 385 mg of 2-amino-5-benzyloxy-3-hydroxymethyl-6-isobutylpyrazine 1-oxide (Compound B-11) as pale yellow fine needle-like crystals having a melting point of 129.0°-131.3° C.

Workup

  1. additionAfter completion of the dropwise addition
  2. customwas returned to room temperature
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customThe residue was purified by a silica gel column chromatography (eluting solvent: 70% by volume of methanol-dichloromethane)
  7. customfollowed by recrystallization from benzene

Sources & evidence

ORD record
ord-29edabfe2cb744fb808d05be378daa00
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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