Water → HCID 86734167, compound

HRID 1730141Notes

Reaction equation

HRID 1730141 reaction equation
[C@@H:1]1([N:9]2[CH:14]=[CH:13][N+:12]([O-:15])=[CH:11][C:10]2=[O:16])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.N1[CH:22]=[CH:21]C=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].[OH2:30]>>[C:23]([O:4][C@@H:3]1[C@@H:5]([CH2:7][O:8][C:21](=[O:30])[CH3:22])[O:6][C@H:1]([N:9]2[CH:14]=[CH:13][N+:12]([O-:15])=[CH:11][C:10]2=[O:16])[CH2:2]1)(=[O:25])[CH3:24]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13604374HCID 13604374, compound

Product 1

HCID 86734167HCID 86734167, compound

Procedure

A solution of 200 mg of 1,2-dihydro-1-(2deoxy-β-D-erythro-pentofuranosyl)-2-oxopyrazine 4-oxide (Berkowitz et al., Journal of Medicinal Chemistry, 1973, Volume 16, No. 2., pages 183-184) in 4 ml. of pyridine was treated at room temperature with 0.2 ml. of acetic anhydride. After standing overnight, the reaction mixture was treated in the cold with water, extracted into methylene chloride and washed with dilute HCl and 5% NaHCO3. Removal of the dried solvent left the diacetate which was purified by column chromatography on silica gel.

Workup

  1. extractionextracted into methylene chloride
  2. washwashed with dilute HCl and 5% NaHCO3
  3. customRemoval of the dried solvent
  4. waitleft the diacetate which
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-27276bfdf20f425fa65d79fcba5dbf30
Source dataset
uspto-grants-1976_11
Patent number
US03991185

Reaction notes

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