Ammonia → HCID 5271807, compound

HRID 392316Notes

Reaction equation

HRID 392316 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[C:5](=[O:12])[N:4]([C@H:13]2[C@H:17]([OH:18])[C@H:16]([OH:19])[C@H:15]([CH2:20][OH:21])[O:14]2)[CH:3]=1.[NH3:22]>CO>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:22])=[O:9])[C:5](=[O:12])[N:4]([C@H:13]2[C@H:17]([OH:18])[C@H:16]([OH:19])[C@@H:15]([CH2:20][OH:21])[O:14]2)[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69761827HCID 69761827, compound

Product 1

HCID 5271807HCID 5271807, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 4 mL of methanol was dissolved 0.26 g of methyl 6-chloro-4-[(2R,3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxylate. While cooling the solution with ice, gaseous ammonia was introduced until saturation. The reaction mixture was stirred at an ice-cooled temperature for one hour and then the solvent was removed under reduced pressure. By purifying the residue thus obtained by column chromatography [eluent: chloroform:methanol=7:1], 0.06 g of 6-chloro-4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxamide was obtained as a light yellow-colored solid product.

Workup

  1. additionwas introduced until saturation
  2. temperaturecooled temperature for one hour
  3. customthe solvent was removed under reduced pressure
  4. customBy purifying the residue
  5. customthus obtained by column chromatography [eluent: chloroform:methanol=7:1]

Sources & evidence

ORD record
ord-6f5bd1c9297b4a509679452c26a3e691
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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