Methanol → HCID 9957988, compound

HRID 748491Notes

Reaction equation

HRID 748491 reaction equation
CO.[F:3][C:4]1[CH:36]=[CH:35][C:7]2[S:8][C:9]([S:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][CH:24]=[C:25]([C:27]([O:29]C)=[O:28])[N:26]=4)=[CH:18][C:17]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:14])=[O:13])=[C:10]([CH3:11])[C:6]=2[CH:5]=1.[OH-].[Na+]>O>[F:3][C:4]1[CH:36]=[CH:35][C:7]2[S:8][C:9]([S:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[O:23][CH:24]=[C:25]([C:27]([OH:29])=[O:28])[N:26]=4)=[CH:18][C:17]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:13])=[O:14])=[C:10]([CH3:11])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12045143HCID 12045143, compound

Product 1

HCID 9957988HCID 9957988, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into 150 mL of methanol was dissolved 7.85 g of Compound 23, and 15 mL of 10% aqueous sodium hydroxide solution and 15 mL of water were added thereto at room temperature, followed by 15 minutes of stirring. The precipitated crystals were dissolved by adding 90 mL of water, and the solution was stirred at the same temperature for 17 hours. After the solvent was removed by evaporation, 45 mL of 1 mol/L hydrochloric acid was added to the residue, the precipitated crystals were collected by filtration and washed with water, and 100 mL of DMF was added to the resulting crude crystals, followed by heating under refluxing. After filtration at a hot state, 70 mL of ethanol was added and recrystallization was carried out. The resulting crystals were collected by filtration, washed several times with ethanol and water alternatively, and dried over diphosphorus pentoxide under reduced pressure to obtain 5.78 g of the title compound as colorless powder.

Workup

  1. additionwere added
  2. dissolutionThe precipitated crystals were dissolved
  3. stirringthe solution was stirred at the same temperature for 17 hours
  4. customAfter the solvent was removed by evaporation, 45 mL of 1 mol/L hydrochloric acid
  5. additionwas added to the residue
  6. filtrationthe precipitated crystals were collected by filtration
  7. washwashed with water, and 100 mL of DMF
  8. additionwas added to the resulting crude crystals
  9. temperatureby heating
  10. temperatureunder refluxing
  11. filtrationAfter filtration at a hot state, 70 mL of ethanol
  12. additionwas added
  13. customrecrystallization
  14. filtrationThe resulting crystals were collected by filtration
  15. washwashed several times with ethanol and water alternatively
  16. dry with materialdried over diphosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-271d2986603f46d783fa9e4c0fedfde8
Source dataset
uspto-grants-2008_07
Patent number
US07399781B2

Reaction notes

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