Acetic Anhydride → HCID 13451547, compound

HRID 1728979Notes

Reaction equation

HRID 1728979 reaction equation
[CH3:1][O:2][C:3]([C@H:5]([C@H:14](C)[CH2:15][CH3:16])[CH2:6][CH:7](C(O)=O)C(O)=O)=[O:4].C([O-])(=[O:20])C.[Na+].C(OC(=O)C)(=O)C>>[CH3:1][O:2][C:3]([C@@H:5]1[C@H:6]([CH3:7])[CH2:16][C:15](=[O:20])[CH2:14]1)=[O:4]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 57143514HCID 57143514, compound

Product 1

HCID 13451547HCID 13451547, compoundYield 106.5%

Procedure

3.8 g of (3S, 4R)-3-methoxycarbonyl-4-methylhexane dicarboxylic acid and 1.1 g of sodium acetate were added to 18 ml of acetic anhydride, and the mixture was refluxed for one hour. The reaction mixture was cooled down to room temperature, and then allowed to stand for one hour at 5° C. The resulting precipitate was filtered off, and the filtrate was concentrated. To the residue was added ethyl acetate, and after the insoluble material was filtered off, the filtrate was concentrated. The residue was purified by distillation under a reduced pressure, and thus 2.23 g of the titled compound was obtained.

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionTo the residue was added ethyl acetate
  5. filtrationafter the insoluble material was filtered off
  6. concentrationthe filtrate was concentrated
  7. distillationThe residue was purified by distillation under a reduced pressure

Sources & evidence

ORD record
ord-906157dd436647f4894fec9b08dfa826
Source dataset
uspto-grants-1994_07
Patent number
US05329042

Reaction notes

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