Potassium Carbonate → HCID 18969307, compound

HRID 1411908Notes

Reaction equation

HRID 1411908 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[N+:19]([C:22]1[N:23]=[CH:24][NH:25][CH:26]=1)([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:19]([C:22]1[N:23]=[CH:24][N:25]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH:26]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178526856HCID 178526856, compound

Product 1

HCID 18969307HCID 18969307, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 243a (7.0 g, 25.1 mmol), DMF (120 mL), 4-nitro-1H-imidazole (2.80 g, 25.1 mmol), and K2CO3 (6.9 g, 50.2 mmol). The mixture was heated at 120° C. for overnight. After this time the reaction was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The residue was purified by silica-gel column chromatography eluting with 2:2:1 ethyl acetate/petroleum ether/dichloromethane to afford 243b (2.4 g, 32.4%) as a yellow solid. MS-ESI: [M+H]+ 297.3

Workup

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. temperatureAfter this time the reaction was cooled to room temperature
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 2:2:1 ethyl acetate/petroleum ether/dichloromethane

Sources & evidence

ORD record
ord-4560797555b84157a65653ff22c68217
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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