HCID 178525214, compound → HCID 68764704, compound

HRID 1615760Notes

Reaction equation

HRID 1615760 reaction equation
C([N:8]([CH:21]([CH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)[C:22]([O-])=[O:23])[CH2:9]/[C:10](/[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=1)=[N:11]\O)C1C=CC=CC=1>C(O)C.[Pd]>[F:20][C:15]1[CH:14]=[C:13]([CH:10]2[NH:11][C:22](=[O:23])[CH:21]([CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[NH:8][CH2:9]2)[CH:18]=[C:17]([F:19])[CH:16]=1

Participants

4

Reactant 1

HCID 178525214HCID 178525214, compound

Product 1

HCID 68764704HCID 68764704, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4.2 g (9.4 mmol) ethyl (rac)-E/Z-{benzyl-[2-(3,5-difluoro-phenyl)-2-hydroxyimino-ethyl]-amino}-(tetrahydro-pyran-4-yl)-acetate in 100 ml of ethanol were hydrogenated under a hydrogen atmosphere together with 0.80 g of 10% palladium charcoal for 20 h at 50° C. More catalyst was added and the mixture was hydrogenated at 70° C. The catalyst was removed by suction filtering and the solvent was evaporated down. The residue was dissolved in ethanol, combined with 2 g sodium hydrogen carbonate and refluxed overnight. After cooling the insoluble constituents of the reaction mixture were suction filtered. The filtrate was evaporated down. The residue was purified by flash chromatography. The fractions were evaporated down and the residue was triturated with diisopropylether. The precipitate was suction filtered and dried.

Workup

  1. additionMore catalyst was added
  2. customwas hydrogenated at 70° C
  3. customThe catalyst was removed by suction
  4. filtrationfiltering
  5. customthe solvent was evaporated down
  6. dissolutionThe residue was dissolved in ethanol
  7. temperaturerefluxed overnight
  8. temperatureAfter cooling the insoluble constituents of the reaction mixture
  9. customThe filtrate was evaporated down
  10. customThe residue was purified by flash chromatography
  11. customThe fractions were evaporated down
  12. customthe residue was triturated with diisopropylether
  13. filtrationfiltered
  14. customdried

Sources & evidence

ORD record
ord-ab7422dc1aa84124921fd94f37aeddf8
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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