Potassium Carbonate → HCID 86755678, compound

HRID 1872181Notes

Reaction equation

HRID 1872181 reaction equation
[ClH:1].[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[CH2:10]([C@H:17]([NH:26][C:27]([C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][C:34](Cl)=[CH:33][CH:32]=2)=[O:28])[C:18](=[O:25])[N:19]1[CH2:23][CH2:22][C:21](=O)[CH2:20]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C.O>[CH2:10]([C@H:17]([NH:26][C:27]([C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][C:34]([Cl:1])=[CH:33][CH:32]=2)=[O:28])[C:18]([N:19]1[CH2:23][CH2:22][C:21](=[N:2][OH:3])[CH2:20]1)=[O:25])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 57296325HCID 57296325, compound

Product 1

HCID 86755678HCID 86755678, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine hydrochloride (68 mg, 0.82 mmol) and potassium carbonate (136 mg, 0.98 mmol) were added to a solution of 5-chloro-1H-indole-2-carboxylic acid [(1S)-benzyl-2-oxo-2-(3-oxo-pyrrolidin-1-yl)-ethyl]-amide in ethanol (5 ml) and water (1 ml) at 25° C. After 48 hours, the reaction mixture was concentrated and the residue dissolved in ethyl acetate. The resulting solution was washed two times with water and once with brine, dried over Na2SO4, and concentrated. Two substances appearing to be syn/anti oxime isomers separated by chromatography on silica eluted with 2.5%, 5%, and 10% ethanol in dichloromethane.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe resulting solution was washed two times with water
  4. dry with materialonce with brine, dried over Na2SO4
  5. concentrationconcentrated
  6. customseparated by chromatography on silica
  7. washeluted with 2.5%, 5%, and 10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-7cfd318abd3a44008e398b9a93471897
Source dataset
uspto-grants-2000_08
Patent number
US06107329

Reaction notes

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