Ethanol → HCID 58006841, compound

HRID 1951905Notes

Reaction equation

HRID 1951905 reaction equation
[OH-].[Na+].C(O)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[N:20]3[C:16]([S:17][C:18]([C:24]([O:26]CC)=[O:25])=[C:19]3[CH:21]([CH3:23])[CH3:22])=[N:15][C@:14]2([C:30]2[CH:31]=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[CH3:29])=[CH:9][C:8]=1[F:37]>O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[N:20]3[C:16]([S:17][C:18]([C:24]([OH:26])=[O:25])=[C:19]3[CH:21]([CH3:22])[CH3:23])=[N:15][C@:14]2([C:30]2[CH:31]=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=2)[CH3:29])=[CH:9][C:8]=1[F:37]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 58007160HCID 58007160, compound

Product 1

HCID 58006841HCID 58006841, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1 N aqueous sodium hydroxide solution (6 ml) was added to an ethanol (30 ml) solution of the compound (2.06 g, 4.17 mmol) obtained in Step 12 above and the resulting mixture was stirred under heating at 60° C. for 16 hours. After cooling, the solvent was concentrated under reduced pressure and the residue obtained was diluted with water and then washed with diethyl ether. The aqueous layer was made into an acidic solution by the gradual addition of 1 N aqueous hydrochloric acid solution under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, a diethyl ether/n-hexane mixed solvent was added to the residue and the resulting precipitate was collected by filtration and dried to give the title compound (1.51 g, 87%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customthe residue obtained
  4. washwashed with diethyl ether
  5. additionThe aqueous layer was made into an acidic solution by the gradual addition of 1 N aqueous hydrochloric acid solution under ice cooling
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. additiona diethyl ether/n-hexane mixed solvent was added to the residue
  11. filtrationthe resulting precipitate was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-2c84f880c1f0443abb91708d49a0e46a
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

Loading…