Dimethylformamide → HCID 15882824, compound

HRID 433866Notes

Reaction equation

HRID 433866 reaction equation
CN(C)C=O.[N-:6]=[N+:7]=[N-:8].[Na+].[C:10]([O:13][C@@H:14]1[O:31][C@H:30]([CH2:32]S(C)(=O)=O)[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]1[O:16][C:17](=[O:19])[CH3:18])(=[O:12])[CH3:11]>C(OCC)(=O)C>[C:10]([O:13][C@@H:14]1[O:31][C@H:30]([CH2:32][N:6]=[N+:7]=[N-:8])[C@@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]1[O:16][C:17](=[O:19])[CH3:18])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 54392295HCID 54392295, compound

Product 1

HCID 15882824HCID 15882824, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A 100 mL round bottom flask was charged with 40 mL anhydrous dimethylformamide, sodium azide (2.19 g, 33.6 mmol), and crude 1,2,3,4-tetra-O-acetyl-6-deoxy-6-methanesulfonyl-β-D-glucopyranose (1.9374 g, 4.54 mmol). The resulting homogeneous solution was heated to 70° C. and allowed to react for 10 hours. The reaction was then diluted with 200 mL of ethyl acetate and washed with copious amounts of water. The organic layer was dried over magnesium sulfate, filtered and the solvent removed in vacuo. The resulting brown solid was purified by column chromatography over silica gel to yield 668.3 mg of the title compound (39.5%). MS (FAB) calculated for C14H19N3O9 (M−OCOCH3) 314.1, found 314.1.

Workup

  1. customto react for 10 hours
  2. washwashed with copious amounts of water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe resulting brown solid was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-1db991fc702e4acdb86cc095a9bd3e79
Source dataset
uspto-grants-2003_12
Patent number
US06670324B2

Reaction notes

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