Water → HCID 14860716, compound

HRID 2256006Notes

Reaction equation

HRID 2256006 reaction equation
[C:1]([NH:4][CH:5]([O:16]CC)[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(=[O:3])[CH3:2].B(F)(F)F.CCOCC.O.C([O-])(O)=O.[Na+]>>[C:1]([NH:4][CH:5]([OH:16])[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 14212862HCID 14212862, compound

Product 1

HCID 14860716HCID 14860716, compound

Procedure

Reacting 2-acetamido-N-benzyl-2-ethoxyacetamide (1.00 g, 4.0 mmol), BF3.Et2O (0.91 g, 6.4 mmol) and H2O (0.12 g, 6.7 mmol) followed by aqueous NaHCO3 workup gave an aqueous reaction mixture. The solution was then extracted with EtOAc (3×50 mL), and the combined EtOAc extracts were dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash column chromatography on SiO2 gel (3% MeOH/CHCl3) to give the desired product as a white solid.

Workup

  1. customgave an aqueous reaction mixture
  2. extractionThe solution was then extracted with EtOAc (3×50 mL)
  3. dry with materialthe combined EtOAc extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on SiO2 gel (3% MeOH/CHCl3)

Sources & evidence

ORD record
ord-b0523b51b0c34d368eef8eee0a9f11ed
Source dataset
uspto-grants-1997_08
Patent number
US05654301

Reaction notes

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