Ethyl Acetate → HCID 15080947, compound

HRID 477581Notes

Reaction equation

HRID 477581 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@H:6]1[N:19]=[N+]=[N-])(=[O:3])[CH3:2].[H][H].[C:24](OCC)(=[O:26])[CH3:25]>[Pd]>[C:24]([NH:19][C@@H:6]1[O:7][CH2:8][C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]1[O:4][C:1](=[O:3])[CH3:2])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2725017ST50306943HCID 178418361HCID 178418361, compound

Product 1

HCID 15080947HCID 15080947, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In 20 ml of ethyl acetate was dissolved 0.73 g of 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-xylopyranose, and 65 mg of 10% Pd/C was added to the solution. Then the solution was stirred in a hydrogen atmosphere for 2 hours. The Pd/C was removed by filtration, and the filtrate was concentrated. To the concentrate was added 20 ml of pyridine, 3 ml of acetic anhydride and then 10 mg of 4-dimethylaminopyridine, and the mixture was stirred for 16 hours. Water was added to the reaction, and the mixture was extracted with chloroform. The chloroform layer was washed with 0.1 N HCl solution, 1% sodium bicarbonate solution and finally with water, dehydrated and concentrated. The residue was subjected to silica gel column chromatography with a system of chloroform-acetone (100:1) to obtain 0.4 mg of 1-acetamido-2,3,4-tri-O-acetyl-1-deoxy-β-D-xylopyranose.

Workup

  1. additionwas added to the solution
  2. customThe Pd/C was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionTo the concentrate was added 20 ml of pyridine, 3 ml of acetic anhydride
  5. additionWater was added to the reaction
  6. extractionthe mixture was extracted with chloroform
  7. washThe chloroform layer was washed with 0.1 N HCl solution, 1% sodium bicarbonate solution and finally with water
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-abf8a18776d74fac8ee5c29c0bdd667e
Source dataset
uspto-grants-1989_12
Patent number
US04888418

Reaction notes

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