Hydrochloric Acid → HCID 59079565, compound

HRID 392314Notes

Reaction equation

HRID 392314 reaction equation
C([O:4][CH2:5][C@@H:6]1[C@@H:10]([O:11]C(=O)C)[CH2:9][CH:8]([N:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH2:23])=[O:22])[C:16]2=[O:24])[O:7]1)(=O)C.C[O-].[Na+].Cl>CO>[OH:11][C@@H:10]1[C@@H:6]([CH2:5][OH:4])[O:7][CH:8]([N:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH2:23])=[O:22])[C:16]2=[O:24])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 69758184HCID 69758184, compound

Product 1

HCID 59079565HCID 59079565, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 2 ml of methanol was dissolved 0.20 g of {(2R,3S)-3-(acetyloxy)-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]tetrahydro-2-furanyl}methyl acetate. While cooling the solution with ice, 0.23 g of 28% methanol solution of sodium methoxide was added, and stirred for 20 minutes. Then, 1.2 ml of 1 mol/L hydrochloric acid was added to the reaction mixture, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography [eluent: chloroform:methanol=10:1] to obtain 90 mg of 4-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxamide as a yellow oily product.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by column chromatography [eluent: chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-2bd8028b74984ebd8f3212e9fa456de4
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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