Ammonium Chloride → HCID 86654263, compound

HRID 42151Notes

Reaction equation

HRID 42151 reaction equation
CS([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:9][N:8]=1)(=O)=O.[S:26]([C:30]1[CH:35]=[CH:34][C:33]([O-])=[CH:32][CH:31]=1)(=[O:29])(=[O:28])[NH2:27].[K+].[Cl-].[NH4+]>CS(C)=O>[S:26]([C:30]1[CH:35]=[CH:34][C:33]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)=[CH:9][N:8]=2)=[CH:32][CH:31]=1)(=[O:29])(=[O:28])[NH2:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67083060Potassium 4-sulfamoylphenolateHCID 86654264Tert-butyl 4-[2-(methanesulfonyloxymethyl)pyridin-5-yl]piperidine-1-carboxylate

Product 1

HCID 86654263HCID 86654263, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl 4-[2-(methanesulfonyloxymethyl)pyridin-5-yl]piperidine-1-carboxylate (Example 1(3)) (24 mg, 0.065 mmol) in dimethyl sulfoxide (1 mL) was added potassium 4-sulfamoylphenolate (14 mg, 0.065 mmol). The mixture was stirred at room temperature for 3.5 hours, to which was added saturated aqueous ammonium chloride solution and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/8 and chloroform/methanol=200/1→20/1) to give the title compound as a white crystal (16 mg, yield 54%).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/8 and chloroform/methanol=200/1→20/1)

Sources & evidence

ORD record
ord-60c14c363c0549d4b508eebe4cf55d25
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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