Hydrochloric Acid → HCID 5271821, compound

HRID 392315Notes

Reaction equation

HRID 392315 reaction equation
C([O:9][CH2:10][C@@H:11]1[C@@H:15]([O:16]C(=O)C2C=CC=CC=2)[C@@H:14]([O:25]C(=O)C2C=CC=CC=2)[C@H:13]([N:34]2[CH:39]=[C:38]([F:40])[N:37]=[C:36]([C:41]([NH2:43])=[O:42])[C:35]2=[O:44])[O:12]1)(=O)C1C=CC=CC=1.C[O-].[Na+].Cl>CO>[OH:25][C@@H:14]1[C@H:15]([OH:16])[C@@H:11]([CH2:10][OH:9])[O:12][C@H:13]1[N:34]1[CH:39]=[C:38]([F:40])[N:37]=[C:36]([C:41]([NH2:43])=[O:42])[C:35]1=[O:44]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 12149203HCID 12149203, compound

Product 1

HCID 5271821HCID 5271821, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 2.0 mL of methanol was dissolved 0.15 g of [(2R,3R,4R,5R)-5-[3-(aminocarbonyl)-5-fluoro-2-oxo-1(2H)-pyrazinyl]-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate. Then, 0.14 g of a 28% methanolic solution of sodium methoxide was added and stirred at an ice-cooled temperature for 20 minutes and thereafter at room temperature for 30 minutes. The reaction mixture was acidified with 0.75 mL of 1 mol/L hydrochloric acid and the solvent was removed under reduced pressure. After purifying the residue by column chromatography [eluent: chloroform:methanol=5:1], isopropanol and diethyl ether were added and the solid product was collected by filtration to obtain 40 mg of 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxamide.

Workup

  1. temperaturecooled temperature for 20 minutes
  2. customthe solvent was removed under reduced pressure
  3. customAfter purifying the residue by column chromatography [eluent: chloroform:methanol=5:1], isopropanol and diethyl ether
  4. additionwere added
  5. filtrationthe solid product was collected by filtration

Sources & evidence

ORD record
ord-35d8b4af6e2f4ef8ae3449bec221e234
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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