Hydrochloric Acid → HCID 19739760, compound

HRID 2255165Notes

Reaction equation

HRID 2255165 reaction equation
C(Cl)(=O)OCC.[CH2:7]([C:11]1[C:12](=[O:23])[NH:13][C:14]([C:20](O)=[O:21])=[C:15]([O:18][CH3:19])[N+:16]=1[O-:17])[CH:8]([CH3:10])[CH3:9].[BH4-].[Li+].Cl>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[OH:21][CH2:20][C:14]1[NH:13][C:12](=[O:23])[C:11]([CH2:7][CH:8]([CH3:10])[CH3:9])=[N+:16]([O-:17])[C:15]=1[O:18][CH3:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4148881Lithium borohydrideHCID 15292775HCID 15292775, compound

Product 1

HCID 19739760HCID 19739760, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.70 Milliliters of ethyl chlorocarbonate was added, at -15° C., to a solution of 730 mg of 3-isobutyl-5-methoxy-1,2-dihydropyrazin-2-one-6-carboxylic acid 4-oxide and 1.0 ml of triethylamine dissolved in 20 ml of tetrahydrofuran, and the mixture was stirred for 2 hours at the same temperature. Thereto was added 330 mg of lithium borohydride, and the mixture was stirred for 18 hours at room temperature. To the reaction mixture was added 5 ml of 10% hydrochloric acid, and the mixture was diluted with ethyl acetate with stirring, and the resulting mixture was dried over magnesium sulfate, then the solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (eluting solvent: 10% by volume of methanol-chloroform) to obtain 467 mg of 6-hydroxymethyl-3-isobutyl-5-methoxy-1,2-dihydropyrazin-2-one 4-oxide (Compound B-35) as a pale yellow oily substance.

Workup

  1. stirringthe mixture was stirred for 18 hours at room temperature
  2. stirringwith stirring
  3. dry with materialthe resulting mixture was dried over magnesium sulfate
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by a silica gel column chromatography (eluting solvent: 10% by volume of methanol-chloroform)

Sources & evidence

ORD record
ord-3d73baf679a244c48c542791728165d1
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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