Water → HCID 66941872, compound

HRID 348728Notes

Reaction equation

HRID 348728 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]3[C:24](=[O:25])C4C(=CC=CC=4)C3=O)=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.[OH2:27].NN.O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CO.C1COCC1.C(OCC)(=O)C>[C:8]([O:27][C:24](=[O:25])[NH:16][CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[S:10][C:6]([CH2:4][OH:5])=[CH:7][C:8]=2[CH:14]=1)([CH3:14])([CH3:9])[CH3:7]

Participants

8

Reactant 4

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 21226445Aluminium lithium hydrideHCID 66941854HCID 66941854, compound

Product 1

HCID 66941872HCID 66941872, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (1.05 g) obtained in Example 120-1 was dissolved in methanol (20 ml) and added with hydrazine monohydrate (1.0 ml), followed by thermal reflux for 3 hours. The solution was added with water and subjected to extraction with chloroform. The resulting organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. The dried product was dissolved in DMF (30 ml) and then added with triethylamine (0.60 ml) and di-t-butyl dicarbonate (942.8 mg), followed by stirring overnight at room temperature. After the solvent had been distilled off, the residue was added with water and extracted with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. The dried product was dissolved in anhydrous THF (10 ml). The solution was gradually dropped in a solution cooled at 0° C., which was prepared by suspending lithium aluminum hydride (218.6 mg) in anhydrous THF (20 ml), over 5 minutes, followed by stirring at 0° C. for 1 hour. Ethyl acetate and methanol were added to the solution, and the whole was concentrated. The residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (600.0 mg) as a white solid.

Workup

  1. temperatureby thermal reflux for 3 hours
  2. extractionsubjected to extraction with chloroform
  3. washThe resulting organic layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. dissolutionThe dried product was dissolved in DMF (30 ml)
  6. additionadded with triethylamine (0.60 ml) and di-t-butyl dicarbonate (942.8 mg)
  7. distillationAfter the solvent had been distilled off
  8. additionthe residue was added with water
  9. extractionextracted with chloroform
  10. washThe organic layer was washed with saturated saline solution
  11. dry with materialdried with anhydrous sodium sulfate
  12. dissolutionThe dried product was dissolved in anhydrous THF (10 ml)
  13. additionThe solution was gradually dropped in a solution
  14. temperaturecooled at 0° C.
  15. customwhich was prepared
  16. waitover 5 minutes
  17. stirringby stirring at 0° C. for 1 hour
  18. concentrationthe whole was concentrated
  19. customThe residue was then purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-93f17baf38e54276b24bff8e1a47f8d2
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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