Potassium Carbonate → HCID 67332517, compound

HRID 1942529Notes

Reaction equation

HRID 1942529 reaction equation
Cl[C:2]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:5]([C:6]([N:8]([CH:22]([CH3:24])[CH3:23])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[O:7])=[C:4]([CH3:30])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br-].[Mg+2].[Br-].[S-2:40].[Li+].[Li+].Br[C:44]([CH3:57])([CH3:56])[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:46]>CS(C)=O>[CH3:56][C:44]([S:40][C:2]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:5]([C:6]([N:8]([CH:22]([CH3:24])[CH3:23])[C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[O:7])=[C:4]([CH3:30])[CH:3]=1)([CH3:57])[C:45]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:46]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 82241Magnesium BromideHCID 10290727Dilithium SulfideHCID 22015096HCID 22015096, compoundHCID 58376495HCID 58376495, compound

Product 1

HCID 67332517HCID 67332517, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl (3R)-3-[(4-chloro-2-methyl-5-nitrobenzoyl)(isopropyl)amino]-piperidine-1-carboxylate (5 g) in dimethylsulfoxide (55 ml) were added potassium carbonate (4.7 g), magnesium bromide.diethyl etherate (3.5 g), lithium sulfide (0.78 g), and the mixture was stirred at room temperature. Two hours later, to the reaction solution was added octyl 2-bromoisobutyrate (4.7 g), and the mixture was stirred at 60° C. for one hour. The reaction mixture was cooled to room temperature, and filtered on celite. To the filtrate was added a saturated aqueous sodium hydrogen carbonate solution (150 ml), and the mixture was extracted twice with ethyl acetate (100 ml). The combined organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=3/1) to give the title compound (4.9 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered on celite
  3. additionTo the filtrate was added a saturated aqueous sodium hydrogen carbonate solution (150 ml)
  4. extractionthe mixture was extracted twice with ethyl acetate (100 ml)
  5. washThe combined organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-8004710ebcf245a0bb2a933d30d72f5a
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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