Methanol → HCID 23144787, compound

HRID 337480Notes

Reaction equation

HRID 337480 reaction equation
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:7][C:6]=1[C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)(=[O:4])[CH:2]=[CH2:3].[OH-:23].[K+].O.[CH3:26]O>>[O:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[C:6]1[N:7]=[C:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[S:9][C:5]=1[C:1]([CH2:2][CH2:3][O:23][CH3:26])=[O:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 23144605HCID 23144605, compound

Product 1

HCID 23144787HCID 23144787, compound

Procedure

Compound 408 (110 mg, 0.343 mmol) was dissolved in methanol (10 mL), and potassium hydroxide (20.0 mg, 0.356 mmol) was added thereto, followed by stirring under heating and reflux for 2.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the entitled Compound 409 (124 mg, 0.343 mmol).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 2.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-92deaf2523d344ebbd80e5b2ac0d6538
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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