Dimethylformamide → HCID 71279203, compound

HRID 1621115Notes

Reaction equation

HRID 1621115 reaction equation
C(OC([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.Br[CH2:41][CH2:42][O:43][CH3:44]>C(OCC)(=O)C>[CH3:44][O:43][CH2:42][CH2:41][N:15]1[C:11]([CH2:10][CH2:9][NH:8][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[N:12][C:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:14]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 809722-Bromoethyl methyl ether2×HCID 71279243HCID 71279243, compound

Product 1

HCID 71279203HCID 71279203, compoundYield 140.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-[2-Bis(tert-butoxycarbonyl)aminoethyl]-3-phenyl-[1,2,4]triazole (96 mg, 247 μmol; example 22, step 1) and potassium carbonate (85.4 mg, 618 μmol) were combined with DMF (1 mL) and the mixture was stirred for 30 min at RT. 1-Bromo-2-methoxyethane (34.3 mg, 23.2 μL, 247 μmol) was added and the mixture was stirred at 60° C. for 16 h. The reaction mixture was cooled down to RT, a second portion of 1-bromo-2-methoxyethane (34.3 mg, 23.2 μL, 247 μmol) and potassium carbonate (34.2 mg, 247 μmol) were added and the mixture was stirred at 60° C. for another 4 h. The reaction mixture was poured into ethyl acetate (25 mL) and the organic phase was washed with water (3×10 mL) and brine (1×15 mL). The aqueous layers were back-extracted with ethyl acetate (1×25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to give 120 mg crude product. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless oil (29 mg, 83.7 μmol, 33.9%).

Workup

  1. stirringthe mixture was stirred at 60° C. for 16 h
  2. temperatureThe reaction mixture was cooled down to RT
  3. stirringthe mixture was stirred at 60° C. for another 4 h
  4. washthe organic phase was washed with water (3×10 mL) and brine (1×15 mL)
  5. extractionThe aqueous layers were back-extracted with ethyl acetate (1×25 mL)
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10f0e31768844ac580fc82aa4e1d3606
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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