Potassium Hydroxide → HCID 22325564, compound

HRID 496312Notes

Reaction equation

HRID 496312 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH3:24])=[C:17]([C:25]3[NH:39][C:28]4[N:29]([CH2:36][CH2:37][CH3:38])[C:30](=[O:35])[N:31]([CH3:34])[C:32](=[O:33])[C:27]=4[CH:26]=3)[CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)(C)C>[CH3:34][N:31]1[C:32](=[O:33])[C:27]2[CH:26]=[C:25]([C:17]3[CH:16]=[C:15]([S:12]([N:9]4[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]4)(=[O:14])=[O:13])[CH:20]=[CH:19][C:18]=3[O:21][CH2:22][CH2:23][CH3:24])[NH:39][C:28]=2[N:29]([CH2:36][CH2:37][CH3:38])[C:30]1=[O:35]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69736934HCID 69736934, compound

Product 1

HCID 22325564HCID 22325564, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of the title compound of Example 86 (0.5 g, 0.89 mmol) and potassium hydroxide (0.58 g, 8.90 mmol, 85%) in isopropanol (20 mL) was refluxed for 18 h. The resulting mixture was evaporated under reduced pressure and the resulting residue was acidified with 6N hydrochloric acid. Then it was basified with aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic extracts were dried (MgSO4) and evaporated under reduced pressure. The resulting crude residue was purified by flash column chromatography on silica-gel (dichloromethane-ethanol-ammonium hydroxide 180:8:1) to yield the title compound (0.24 g, 55%) as a white solid.

Workup

  1. temperaturewas refluxed for 18 h
  2. customThe resulting mixture was evaporated under reduced pressure
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe resulting crude residue was purified by flash column chromatography on silica-gel (dichloromethane-ethanol-ammonium hydroxide 180:8:1)

Sources & evidence

ORD record
ord-0bc77de0ce244618b7e7b9c24382950f
Source dataset
uspto-grants-2005_09
Patent number
US06943253B2

Reaction notes

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