Water → HCID 178492501, compound

HRID 70064Notes

Reaction equation

HRID 70064 reaction equation
C1(S([N:10]2[CH:14]=[C:13]([C:15]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)=[O:16])[N:12]=[C:11]2[C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[N:34](S(C2C=CC=CC=2)(=O)=O)[C:33]([C:47](=[O:60])[C:48]2[CH:53]=[C:52]([O:54][CH3:55])[C:51]([O:56][CH3:57])=[C:50]([O:58][CH3:59])[CH:49]=2)=[CH:32]3)(=O)=O)C=CC=CC=1.[OH-].[Na+].O>C(O)C>[CH3:24][O:23][C:21]1[CH:22]=[C:17]([CH:18]=[C:19]([O:27][CH3:28])[C:20]=1[O:25][CH3:26])[C:15]([C:13]1[N:12]=[C:11]([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[NH:34][C:33]([C:47]([C:48]2[CH:49]=[C:50]([O:58][CH3:59])[C:51]([O:56][CH3:57])=[C:52]([O:54][CH3:55])[CH:53]=2)=[O:60])=[CH:32]3)[NH:10][CH:14]=1)=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58477868(1-(phenylsulfonyl)-2-(1-(phenylsulfonyl)-2-(3,4,5-trimethoxybenzoyl)-1H-indol-5-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

Product 1

HCID 178492501HCID 178492501, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1-(phenylsulfonyl)-2-(1-(phenylsulfonyl)-2-(3,4,5-trimethoxybenzoyl)-1H-indol-5-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone (16xaa) (1 mmol) in ethanol (20 mL) was added sodium hydroxide (10 equiv) and stirred overnight in darkness. The reaction mixture was diluted by 50 mL of water and extracted by ethyl acetate (250 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane:ethyl acetate 3:1) or recrystallized from water and methanol to give a white solid. Yield: 30-95%.

Workup

  1. extractionextracted by ethyl acetate (250 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (hexane:ethyl acetate 3:1)
  5. customrecrystallized from water and methanol
  6. customto give a white solid

Sources & evidence

ORD record
ord-df5634287b594f1fa35e20f4fa17c6a8
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

Loading…