Acetic Anhydride → HCID 69077574, compound

HRID 1785262Notes

Reaction equation

HRID 1785262 reaction equation
[C:1]([C@H:5]1[O:9][C:8](=[O:10])[C@@:7]([C@H:17]2[CH2:21][C:20](=[O:22])[C@H:19]([OH:23])[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)([CH3:4])([CH3:3])[CH3:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1.C(OCC)(=O)C>[C:24]([O:23][C@@H:19]1[CH2:18][C@@H:17]([C@@:7]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8](=[O:10])[O:9][C@H:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[O:6]2)[CH2:21][C:20]1=[O:22])(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 69081664HCID 69081664, compound

Product 1

HCID 69077574HCID 69077574, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 32 mg of (2R,5R)-2-(t-butyl)-5-((1R,3R)-3-hydroxy-4-oxocyclopentyl)-5-phenyl-1,3-dioxolan-4-one in 1 ml of pyridine, 0.5 ml of acetic anhydride was added, followed by 1 hour's stirring at room temperature. The reaction liquid was diluted with ethyl acetate, washed successively with water, 1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the residue obtained was purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/acetone=20/1) to provide 27 mg of the title compound as a colorless oily substance.

Workup

  1. customThe reaction liquid
  2. washwashed successively with water, 1N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue obtained
  6. customwas purified on preparative thin layer chromatography (Kieselgel™ 60F254, Art 5744 (Merck), chloroform/acetone=20/1)

Sources & evidence

ORD record
ord-4c59b96b22fe43faa9b95c584f793fef
Source dataset
uspto-grants-2009_03
Patent number
US07504432B2

Reaction notes

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