Ethanol → HCID 58007160, compound

HRID 1951904Notes

Reaction equation

HRID 1951904 reaction equation
Cl[CH:2]([C:8](=O)[CH:9]([CH3:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]2[NH:27][C:26](=[S:28])[NH:25][C@:24]2([C:30]2[CH:31]=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[CH3:29])=[CH:19][C:18]=1[F:37]>C(OCC)(=O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]2[N:27]3[C:26]([S:28][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]3[CH:9]([CH3:11])[CH3:10])=[N:25][C@:24]2([C:30]2[CH:31]=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[CH3:29])=[CH:19][C:18]=1[F:37]

Participants

5

Reactant 3

HCID 702EthanolHCID 9877606Ethyl 2-chloro-4-methyl-3-oxopentanoateHCID 58007237HCID 58007237, compound

Product 1

HCID 58007160HCID 58007160, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-chloro-4-methyl-3-oxopentanoate (1.36 g, 7.09 mmol) was added to an ethanol (20 ml) solution of the compound (1.94 g, 5.45 mmol) obtained in Step 11 above at room temperature and the resulting mixture was heated to reflux for 16 hours. The reaction mixture was returned to room temperature and the reaction solvent was evaporated under reduced pressure. The residue obtained was diluted with ethyl acetate and the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=3:1 (v/v)] to give the title compound (2.06 g, 76%) as a colorless solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 16 hours
  3. customwas returned to room temperature
  4. customthe reaction solvent was evaporated under reduced pressure
  5. customThe residue obtained
  6. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue obtained
  10. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=3:1 (v/v)]

Sources & evidence

ORD record
ord-49f0aa9e0a8c40cbab8eaf3e129a1697
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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