Triethylamine → HCID 68479144, compound

HRID 2067713Notes

Reaction equation

HRID 2067713 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[O:10][C:11]([CH2:14]Br)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([N:19](CC)CC)C>C(#N)C>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[O:10][C:11]([CH2:14][C:17]#[N:19])=[CH:12][CH:13]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 89779519HCID 89779519, compound

Product 1

HCID 68479144HCID 68479144, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The tert-butyl((5-(bromomethyl)furan-2-yl)methyl)carbamate (5.8 g, 20 mmol) obtained above and 50 mL of acetonitrile were added into a flask. Triethylamine (2.3 g, 22 mmol) was added thereto dropwise and the reaction mixture was stirred at room temperature for 6 h. After the completion of the reaction, the reaction mixture was washed successively with water and saturated brine. The organic layer was dried, concentrated, and crude product was purified by column chromatograph to give 3.9 g (83.3% yield) of 5-(tert-butoxycarbonylaminomethyl)-furan-2-acetonitrile.

Workup

  1. additionwere added into a flask
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed successively with water and saturated brine
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customcrude product was purified by column chromatograph

Sources & evidence

ORD record
ord-aae1da60bcc240c6a8d7fb445fc176c0
Source dataset
uspto-grants-2012_10
Patent number
US08293895B2

Reaction notes

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