Triacetoxyperiodinane → Ethyl oxo[(2-oxopropyl)amino]acetate

HRID 2200583Notes

Reaction equation

HRID 2200583 reaction equation
[OH:1][CH:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:11]=[C:5]([NH:4][CH2:3][C:2](=[O:1])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 85994322Ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate

Product 1

HCID 57348900Ethyl oxo[(2-oxopropyl)amino]acetateYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-(2-hydroxypropylamino)-2-oxoacetate (2.1 g, 13 mmol) in DCM (30 mL) was added Dess-Martin periodinane (6.2 g, 14.6 mmol) in portions at 0° C. and the resulting mixture was stirred at room temperature for 16 h. The reaction was diluted with DCM and extracted with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried and concentrated to give crude product, which was purified via silica gel chromatography eluting with DCM/methanol (60:1) to give ethyl 2-oxo-2-(2-oxopropylamino)acetate (1.7 g, 81.2% yield) as yellow syrup. LCMS retention time 0.392 min, LCMS MH+ 174.

Workup

  1. extractionextracted with saturated aqueous sodium bicarbonate solution and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto give crude product, which
  5. customwas purified via silica gel chromatography
  6. washeluting with DCM/methanol (60:1)

Sources & evidence

ORD record
ord-63cc3d2ea4cd43f5bf266711f361120a
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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