Sodium Acetate → 4-O-Acetyl-1,5-anhydro-2,3,6-trideoxy-3-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]hex-1-enitol

HRID 2051672Notes

Reaction equation

HRID 2051672 reaction equation
C([O-])(=O)C.[Na+].[F:6][C:7]([F:28])([F:27])[C:8]([NH:10][C@@H:11]1[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([CH3:21])[O:14][C@H:13](Br)[C@@H:12]1OC(=O)C)=[O:9]>[Zn].C(O)(=O)C>[F:28][C:7]([F:6])([F:27])[C:8]([NH:10][C@@H:11]1[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:15]([CH3:21])[O:14][CH:13]=[CH:12]1)=[O:9]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 54522117HCID 54522117, compound

Product 1

HCID 1945094-O-Acetyl-1,5-anhydro-2,3,6-trideoxy-3-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]hex-1-enitolYield 77%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 18 g. of zinc dust and 1.8 g. of cupric sulfate in 60 ml. of 50% aqueous acetic acid containing 25 g. of sodium acetate, 10 g. of the product of Examples 10 and 11 in 10 ml. of acetic acid is added dropwise at -10° C. The reaction is continued for 4 hours at -10° C., after which the zinc dust and copper are removed by filtration, 50 g. of ice is added to the filtrate, and the filtrate is extracted three times with chloroform. The combined extracts are washed with water, a cold saturated sodium hydrogen carbonate solution, and water. After the chloroform solution is dried over anhydrous magnesium sulfate, it is evaporated in vacuo to a heavy syrup. The syrupy residue is crystallized from a mixture of ether-petroleum ether to give 4.7 g. (77% yield) of 3-trifluoroacetamido-4-O-acetyl-1,2,3,6-tetradeoxy-L-lyxo-hex-1-enepyranose.

Workup

  1. additionTo a mixture of 18 g
  2. customafter which the zinc dust and copper are removed by filtration, 50 g
  3. additionof ice is added to the filtrate
  4. extractionthe filtrate is extracted three times with chloroform
  5. washThe combined extracts are washed with water
  6. dry with materialAfter the chloroform solution is dried over anhydrous magnesium sulfate, it
  7. customis evaporated in vacuo to a heavy syrup
  8. customThe syrupy residue is crystallized from a mixture of ether-petroleum ether
  9. customto give 4.7 g

Sources & evidence

ORD record
ord-72585f0e34164afaa3e3992a028f2fe7
Source dataset
uspto-grants-1980_01
Patent number
US04181795

Reaction notes

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