Hydrogen Bromide → HCID 23499865, compound

HRID 411914Notes

Reaction equation

HRID 411914 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([CH3:20])(C)[C:13](N(C)OC)=O)=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.[BrH:21].[C:22](=[O:25])([O-])[OH:23].[Na+]>O>[Br:21][CH2:3][CH2:2][CH2:1][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:20])([CH3:13])[C:22]([OH:23])=[O:25])=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 9943470HCID 9943470, compound

Product 1

HCID 23499865HCID 23499865, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Treat 2-(4-cyclopropanecarbonyl-phenyl)-2-methyl-N-methyl-N-methoxy-propionamide (0.15 g, 0.53 mmol) with 48% HBr (1 mL) for 2 hours at 80° C. Cool to room temperature, dilute with water (5 mL) and neutralize with aqueous sodium hydrogen carbonate until pH 7. Extract with methylene chloride (3×15 mL), dry (Na2SO4), filter and evaporate the solvent in vacuo. Purify by silica gel chromatography (3:1 hexane/ethyl acetate) to give the title compound (0.15 g, 95%).

Workup

  1. extractionExtract with methylene chloride (3×15 mL)
  2. dry with materialdry (Na2SO4)
  3. filtrationfilter
  4. customevaporate the solvent in vacuo
  5. customPurify by silica gel chromatography (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c2fcdac25c854bcfaf3a2a6ce4c5f5ce
Source dataset
uspto-grants-2003_05
Patent number
US06559312B2

Reaction notes

Loading…