Malic Acid → (S)-Zopiclone L-Malate

HRID 44214

Reaction equation

HRID 44214 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C@@H:11]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][N:26]=3)[C:18](=[O:19])[C:13]3[N:14]=[CH:15][CH:16]=[N:17][C:12]2=3)=[O:9])[CH2:4][CH2:3]1.[C:28]([OH:36])(=[O:35])[CH:29]([CH2:31][C:32]([OH:34])=[O:33])[OH:30].CN1CCN(C(OC2N(C3C=CC(Cl)=CN=3)C(=O)C3N=CC=NC2=3)=O)CC1>C(OCC)(=O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C@@H:11]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][N:26]=3)[C:18](=[O:19])[C:13]3[N:14]=[CH:15][CH:16]=[N:17][C:12]2=3)=[O:9])[CH2:4][CH2:3]1.[C:28]([O-:36])(=[O:35])[C@H:29]([CH2:31][C:32]([O-:34])=[O:33])[OH:30]

Participants

5

Reactant 3

HCID 525Malic AcidHCID 5735ZopicloneHCID 969472Eszopiclone

Product 1

HCID 131729768(S)-Zopiclone L-MalateYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
40 °C

Procedure

A 250 mL reactor was charged with 1.5 g (S)-zopiclone and 90 mL of ethyl acetate (EtOAc). The contents were heated to 40° C. to dissolve. A 125 mL flask was charged with 540 mg malic acid and 60 mL of ethyl acetate. The contents were heated to 40° C. and the acid solution was transferred slowly to the zopiclone solution. The reaction was stirred for 3 h. The slurry was filtered and washed with ethyl acetate in an appropriate filter. The wet cake was dried under vacuum, isolated and packaged in appropriate container. Isolated yield=96%.

Workup

  1. dissolutionto dissolve
  2. temperatureThe contents were heated to 40° C.
  3. filtrationThe slurry was filtered
  4. washwashed with ethyl acetate in an appropriate filter
  5. customThe wet cake was dried under vacuum
  6. customisolated
  7. customIsolated yield=96%

Sources & evidence

ORD record
ord-05d6cfdf8a344ea9914c2e7b09dd5921
Source dataset
uspto-grants-2013_09
Patent number
US08541416B2

Linked notes

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