Ethyl Acetate → HCID 11827534, compound

HRID 964351Notes

Reaction equation

HRID 964351 reaction equation
[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:38]C(C)=O)[C:5]([C@@:7]1([CH3:37])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][CH2:8]1)=[O:6].O.NN.C(OCC)(=O)C>C(O)C>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:21])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([OH:38])[C:5]([C@@:7]1([CH3:37])[C@H:12]([C@@H:13]2[O:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[C@:11]2([O:33][C:34]([CH3:36])=[O:35])[CH2:31][O:32][C@@H:10]2[CH2:9][CH2:8]1)=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 10929863HCID 10929863, compound

Product 1

HCID 11827534HCID 11827534, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.85 g of 7-deoxybaccatin III was dissolved in 250 ml of 95% ethanol, and 25 ml of hydrazine monohydrate was added thereto, followed by stirring at room temperature for 7 hours. Ethyl acetate was added to the reaction solution, the resulting mixture was washed successively with water and a saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel thin layer chromatography (a developing solvent; hexane:ethyl acetate=3:2 (v/v)) to yield 3.34 g of the titled compound as colorless crystals.

Workup

  1. washthe resulting mixture was washed successively with water
  2. dry with materiala saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel thin layer chromatography (a developing solvent

Sources & evidence

ORD record
ord-d91dd6e1dfc648389c52877dcec5c714
Source dataset
uspto-grants-1998_06
Patent number
US05767296

Reaction notes

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