Hydrochloric Acid → HCID 14456755, compound

HRID 2352289Notes

Reaction equation

HRID 2352289 reaction equation
[O:1]=[C:2]1[CH2:11][C@@H:10]2[C@@:4]([C:24]([O-:26])=[O:25])([N:5]3[C@H:8]([S:9]2)[C@H:7]([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]3=[O:23])[O:3]1.[Na+].[C:28](OCC)(=O)C.[N+](=C)=[N-].Cl>O.CCOCC>[O:1]=[C:2]1[CH2:11][C@@H:10]2[C@@:4]([C:24]([O:26][CH3:28])=[O:25])([N:5]3[C@H:8]([S:9]2)[C@H:7]([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]3=[O:23])[O:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 9550Diazomethane2×HCID 23686745HCID 23686745, compound

Product 1

HCID 14456755HCID 14456755, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

30 mg of the compound obtained in Example 4 was dissolved in 3 ml water. To this solution 3 ml ethyl acetate and 5 ml of diazomethane in ether were added, while cooling the solution with ice. After adding 83 μl of 1N hydrochloric acid, the resulting mixed solutio was stirred for 30 minutes, while cooling with ice. After 30 minutes of stirring, 8 ml of a solution of diazomethane in ether was added; the resulting mixed solution was stirred for 20 minutes, while cooling with ice. The reaction mixture, after dilution with water, was extracted with ethyl acetate. The organic layer was dried (MgSO4), then the solvent was evaporated under reduced pressure. The resulting residue was passed through a silica gel column and eluted with n-hexane-ethyl acetate (2:1), then the eluted fraction containing the desired product was collected and concentrated under reduced pressure to yield 13.5 mg of the subject compound in the form of a white crystal. Melting point: 182° to 184° C.

Workup

  1. temperaturewhile cooling the solution with ice
  2. additionthe resulting mixed solutio
  3. temperaturewhile cooling with ice
  4. stirringAfter 30 minutes of stirring
  5. additionthe resulting mixed solution
  6. stirringwas stirred for 20 minutes
  7. temperaturewhile cooling with ice
  8. extractionThe reaction mixture, after dilution with water, was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried (MgSO4)
  10. customthe solvent was evaporated under reduced pressure
  11. washeluted with n-hexane-ethyl acetate (2:1)
  12. additionthe eluted fraction containing the desired product
  13. customwas collected
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b12c8ab2f1f4ff0989e47980e5f26ef
Source dataset
uspto-grants-1989_10
Patent number
US04876251

Reaction notes

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