Potassium Carbonate → Eszopiclone

HRID 2427793Notes

Reaction equation

HRID 2427793 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C@@H:17]2[N:26]([C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][N:32]=3)[C:24](=[O:25])[C:19]3[N:20]=[CH:21][CH:22]=[N:23][C:18]2=3)=[O:15])[CH2:10][CH2:9]1.C(N[C@@H](C([O-])=O)CC([O-])=O)(=O)C>O>[CH3:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C@@H:17]2[N:26]([C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][N:32]=3)[C:24](=[O:25])[C:19]3[N:20]=[CH:21][CH:22]=[N:23][C:18]2=3)=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86627066HCID 86627066, compound

Product 1

HCID 969472EszopicloneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.7 ml of a 40% aqueous solution of potassium carbonate were added to a solution of 2 g of (S)-zopiclone N-acetyl-D-aspartate in 18 ml of water in about 30 minutes at room temperature. The slurry was maintained for 1.5 hours at this temperature. The product was isolated by filtration and washed twice with 1.4 ml of water. The product was dried under vacuum at room temperature obtaining 1.29 g of eszopiclone (94%) as a white solid. e.e.: 99.8% by chiral HPLC. Water content: 0.9% w/w. Melting point: 198-201° C. [α]D20: +145° (c 1% w/w acetone).

Workup

  1. temperatureThe slurry was maintained for 1.5 hours at this temperature
  2. customThe product was isolated by filtration
  3. washwashed twice with 1.4 ml of water
  4. customThe product was dried under vacuum at room temperature

Sources & evidence

ORD record
ord-27f0e8703d624f01b810de2ed411faef
Source dataset
uspto-grants-2011_06
Patent number
US07968712B2

Reaction notes

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