Potassium Carbonate → HCID 58424876, compound

HRID 2409403Notes

Reaction equation

HRID 2409403 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7](=[O:14])[C:8]3[CH:9]=[CH:10][CH:11]=[N:12][C:13]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1)(=O)=O>C(#N)C.CN(C)C=O>[O:14]=[C:7]1[NH:6][C:5]2[CH:15]=[CH:16][C:2]([O:1][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[CH:3][C:4]=2[C:13]2[N:12]=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 58424936HCID 58424936, compound

Product 1

HCID 58424876HCID 58424876, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

The compound (60 mg, 0.28 mmol) prepared in step 2 and potassium carbonate (120 mg, 0.85 mmol) were dissolved in acetonitrile (6 ml)/N,N-dimethylformamide (3 ml), added with t-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (240 mg, 0.85 mmol). The resulting mixture was stirred for 3 days at 100˜110° C. and cooled to room temperature. After extraction with chloroform, the reaction mixture was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (chloroform:methanol=10:1) to obtain the title compound (65 mg, yield: 58%, white solid).

Workup

  1. extractionAfter extraction with chloroform
  2. washthe reaction mixture was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-4a8a889f82ba45279d7d5ad68c8fe4aa
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

Loading…