Potassium Carbonate → HCID 118038096, compound

HRID 2272490Notes

Reaction equation

HRID 2272490 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][NH:18][C:17](=[O:21])[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH:39]2[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]2)(=O)=O)=CC=1>COCCOC>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][N:18]([CH:39]2[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]2)[C:17](=[O:21])[CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 118038096HCID 118038096, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Potassium tert-butoxide (5.05 g) was added at room temperature to a DME (70 mL) solution of 4-(benzyloxy)pyridin-2(1H)-one (7.55 g). The reaction mixture was stirred at room temperature for 10 minutes. Then, potassium carbonate (10.4 g) and tert-butyl 4-(((4-methylphenyl)sulfonyl)oxy)piperidine-1-carboxylate (20.0 g) were added thereto, and the mixture was stirred at 100 C for 1 day in a nitrogen atmosphere. Then, DME (30 mL) was added thereto, and the mixture was further stirred during the weekend at 100 C. Saturated saline was added to the reaction mixture, followed by extraction with ethyl acetate twice. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (4.40 g).

Workup

  1. stirringthe mixture was stirred at 100 C for 1 day in a nitrogen atmosphere
  2. stirringthe mixture was further stirred during the weekend at 100 C
  3. additionSaturated saline was added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate twice
  5. washThe obtained organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-20758a1a845c4e84ba77e889087ad3b1
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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