Lithium Carbonate → HCID 68675630, compound

HRID 2233015Notes

Reaction equation

HRID 2233015 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][C:9](=[O:11])[N:8]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=1)=[O:5])[CH3:2].Br[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Li+].[Li+].C(#N)C.CN(C=O)C>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:9](=[O:11])[N:8]([C:12]([CH3:14])([CH3:13])[CH3:15])[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11125Lithium CarbonateHCID 21642BromopinacoloneHCID 21891449acetonitrile N,N-dimethylformamideHCID 135961911HCID 135961911, compound

Product 1

HCID 68675630HCID 68675630, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3.0 g of the product of Step B, 7.41 g of 1-bromo-3,3-dimethyl-2-butanone, and 4.15 g of lithium carbonate in a 2:1 mixture of acetonitrile/DMF (90 mL) was heated at 100° C. for four h. The reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with sat. ammonium chloride solution. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with sat. lithium chloride solution, dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography afforded 1-tert-butyl-4-(3,3-dimethyl-2-oxo-butyl)-5-oxo-4,5-dihydro-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester as a yellow oil. MS (M+H+)=312.3.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with sat. ammonium chloride solution
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic layers were washed with sat. lithium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-6eac4f8729374cc38f4d6e4b5b3901aa
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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