Potassium Carbonate → HCID 58503993, compound

HRID 2407704Notes

Reaction equation

HRID 2407704 reaction equation
Cl.[C:2]1([C:8]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[NH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:23]([O:22][C:21]([NH:20][CH2:19][CH2:18][N:10]1[C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9]1)=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate2×HCID 66989455HCID 66989455, compound

Product 1

HCID 58503993HCID 58503993, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound prepared in Example 120 (0.500 g), tert-butyl 2-bromoethylcarbamate (0.704 g) and potassium carbonate (1.16 g) were suspended in acetonitrile (20 mL) and heated at reflux overnight. Another 0.5 equivalents of tert-butyl 2-bromoethylcarbamate was added and the reaction mixture heated at reflux overnight again. The reaction mixture was cooled to room temperature and partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography to furnish the title compound (0.624 g) having the following physical data.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux overnight again
  5. custompartitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  6. washThe organics were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford the crude material, which
  11. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-935d4d14107542a48767327b4a782327
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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