Ammonia → 4-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-oxopyrazine-2-carboxamide

HRID 392313Notes

Reaction equation

HRID 392313 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]=[CH:38][N:37]=[C:36]([C:40]([NH2:42])=[O:41])[C:35]2=[O:43])[O:12]1)(=O)C1C=CC=CC=1.N>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]=[CH:38][N:37]=[C:36]([C:40]([NH2:42])=[O:41])[C:35]1=[O:43]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69760526HCID 69760526, compound

Product 1

HCID 52718194-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-oxopyrazine-2-carboxamideYield 69.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 4 mL of methanol was dissolved 0.37 g of [(2R,3R,4R,5R)-5-[3-(aminocarbonyl)-2-oxo-1(2H)-pyrazinyl]-3,4-bis(benzoyloxy)tetrahydro-2-furanyl]methyl benzoate. While cooling the solution with ice, gaseous ammonia was introduced until saturation. The reaction mixture was stirred at room temperature for 15 hours, and the solvent was removed under reduced pressure. Methanol was added to the residue, and the precipitate was collected by filtration to obtain 0.12 g of 4-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-oxo-3,4-dihydro-2-pyrazinecarboxamide as a light brown-colored solid product.

Workup

  1. additionwas introduced until saturation
  2. customthe solvent was removed under reduced pressure
  3. additionMethanol was added to the residue
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-2f4d1ddb3b604d65b0209c85d75e0380
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

Loading…