Acetic Anhydride → HCID 22864139, compound

HRID 1378529Notes

Reaction equation

HRID 1378529 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]([CH2:11][C@@H:12]([C@@H:14]([CH2:16][N:17]=[N+:18]=[N-:19])[OH:15])[OH:13])=[O:10]>N1C=CC=CC=1>[CH3:8][C:9]([CH2:11][C@@H:12]([C@@H:14]([CH2:16][N:17]=[N+:18]=[N-:19])[OH:15])[O:13][C:1](=[O:3])[CH3:2])=[O:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14866070HCID 14866070, compound

Product 1

HCID 22864139HCID 22864139, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (25 mL) was added to a solution of methyl-5-azido-2.5-dideoxy-D-ribose (6.2 g, 38 mmol) in pyridine (100 mL). After 4 hours at room temperature, the mixture was concentrated in vacuo. The residue (6 g) was purified by flash chromatography eluting with hexanethylacetate (8:2). Evaporation of the eluting solvent gave the product as an oil (4.9 g, 60% yield). NMR

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue (6 g) was purified by flash chromatography
  3. washeluting with hexanethylacetate (8:2)
  4. customEvaporation of the eluting solvent

Sources & evidence

ORD record
ord-3d12e7cc240342d58fec330de090d673
Source dataset
uspto-grants-1997_09
Patent number
US05668152

Reaction notes

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