Potassium Carbonate → HCID 13371396, compound

HRID 351630Notes

Reaction equation

HRID 351630 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:16]([O:15][C:13](=[O:14])[CH2:12][NH:10][O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 13371396HCID 13371396, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of O-benzylhydroxylamine hydrochloride (5 g, 31.3 mmol) in dry DMF (20 ml) was added tert-butyl 2-bromoacetate (4.7 ml, 1 eq.) and potassium carbonate (4.5 g, 1 eq.). The solution was stirred for 16 h at room temperature. The precipitate was filtered off. The solvent was removed, the residue was dissolved in ethyl acetate and extracted with small portions of 1 N HCl, sodium carbonate solution and brine. After drying over sodium sulfate, the solvent was removed to dryness to give 5.86 g (79%) of the title compound as an oil of sufficient purity. MS 182.1 (M+1-tert-butyl)+

Workup

  1. filtrationThe precipitate was filtered off
  2. customThe solvent was removed
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. extractionextracted with small portions of 1 N HCl, sodium carbonate solution and brine
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent was removed to dryness

Sources & evidence

ORD record
ord-79ddc4ac777a4bba91bc2883f391f6a2
Source dataset
uspto-grants-2004_06
Patent number
US06743790B2

Reaction notes

Loading…