Toluene → HCID 86585684, compound

HRID 2119934Notes

Reaction equation

HRID 2119934 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].C1([NH2:36])CCCCC1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[CH:13]1([C:8]([NH2:36])=[O:7])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:12]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7965CyclohexylamineHCID 53232Lovastatin

Product 1

HCID 86585684HCID 86585684, compoundYield 172.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5 g (0.012 mol) of lovastatin, 6 ml (0.052 mol) of cyclohexylamine and 50 ml of toluene was refluxed for 6 hours. The reaction mixture was cooled to RT and 20 ml of ethyl acetate was added. The mixture was washed with 2N HCl (2×30 ml) and water (2×20 ml). The organic layer was dried with sodium sulfate, filtered and evaporated to a volume of 15 ml. 50 ml of hexane was added and the precipitate was filtered to give 5.5 g of lovastatin cyclohexanamide as a white powder.

Workup

  1. temperaturewas refluxed for 6 hours
  2. washThe mixture was washed with 2N HCl (2×30 ml) and water (2×20 ml)
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated to a volume of 15 ml
  6. addition50 ml of hexane was added
  7. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-49345ad33b89432b9b890b474f914314
Source dataset
uspto-grants-2004_02
Patent number
US06686481B2

Reaction notes

Loading…