Potassium Carbonate → HCID 67330927, compound

HRID 244376Notes

Reaction equation

HRID 244376 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([N:13]([CH:27]([CH3:29])[CH3:28])[C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]2)=[O:12])=[C:4]([CH3:30])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:38]([CH3:49])([C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C)C=O>[CH3:49][C:38]([O:1][C:2]1[CH:3]=[C:4]([CH3:30])[C:5]([C:11](=[O:12])[N:13]([C@@H:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:15]2)[CH:27]([CH3:28])[CH3:29])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])([C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:44]([O:46][CH2:47][CH3:48])=[O:45]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 94944Diethyl bromomethylmalonateHCID 86665013HCID 86665013, compound

Product 1

HCID 67330927HCID 67330927, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the obtained 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (138 g) in N,N-dimethylformamide (1000 ml) were added potassium carbonate (91 g), diethyl 2-bromo-2-methylmalonate (94 g), and the mixture was stirred at 80° C. for 8 hours. The reaction solution was allowed to cool to room temperature, filtered through celite, and to the filtrate were added a 5% aqueous sodium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered through celite
  3. additionto the filtrate were added a 5% aqueous sodium hydrogen sulfate solution and ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried over sodium sulfate
  7. customThe sodium sulfate was removed by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4346f346227443aa9524620d4dff3012
Source dataset
uspto-grants-2014_02
Patent number
US08658639B2

Reaction notes

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