Lopinavir → Lopinavir cyclohexane

HRID 2093560Notes

Reaction equation

HRID 2093560 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH2:9][C:10]([NH:12][C@H:13]([C@@H:21]([OH:45])[CH2:22][C@@H:23]([NH:31][C:32]([C@@H:34]([N:38]2[C:43](=[O:44])[NH:42][CH2:41][CH2:40][CH2:39]2)[CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:11])=[C:6]([CH3:46])[CH:5]=[CH:4][CH:3]=1>ClCCl.C1CCCCC1>[CH3:46][C:6]1[C:7]([O:8][CH2:9][C:10]([NH:12][C@H:13]([C@@H:21]([OH:45])[CH2:22][C@@H:23]([NH:31][C:32]([C@@H:34]([N:38]2[C:43](=[O:44])[NH:42][CH2:41][CH2:40][CH2:39]2)[CH:35]([CH3:37])[CH3:36])=[O:33])[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:11])=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=1.[CH2:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 92727Lopinavir

Product 1

HCID 46866070Lopinavir cyclohexaneYield 167.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent2×

Procedure

Lopinavir (10 gm) was dissolved in dichloromethane (90 ml), methylenedichloride layer was dried over sodium sulfate and distilled off the solvent under vacuum at 45 deg C. to obtain residue. To the residue was added cyclohexane (50 ml), distilled off the solvent and the residue was collected. The residue obtained was taken in cyclohexane (70 ml), stirred for 60 hours at 20-25 deg C., filtered, washed the solid with cyclohexane (20 ml) and dried at 55-60 deg C. for 4 hours to obtain 9.5 gm of lopinavir cyclohexane solvate.

Workup

  1. dry with materialmethylenedichloride layer was dried over sodium sulfate
  2. distillationdistilled off the solvent under vacuum at 45 deg C
  3. customto obtain residue
  4. distillationdistilled off the solvent
  5. customthe residue was collected
  6. customThe residue obtained
  7. filtration, filtered
  8. washwashed the solid with cyclohexane (20 ml)
  9. customdried at 55-60 deg C

Sources & evidence

ORD record
ord-7761202f64bb47d29d21beac7d488366
Source dataset
uspto-grants-2013_05
Patent number
US08445506B2

Reaction notes

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