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

HRID 69088Notes

Reaction equation

HRID 69088 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>[CH2:3]([NH:4][C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:2]([CH3:12])=[O:1]

Participants

5

Reactant 2

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

Product 1

HCID 57348900Ethyl oxo[(2-oxopropyl)amino]acetateYield 87.03%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate (10.7 g, 61.07 mmol) in DCM (100.0 mL), is added Dess Martin periodinane (25.9 g, 61.07 mmol) at 0° C. The reaction mixture is stirred at room temperature for 2 hours, diluted with water (100 mL) at 0° C., and extracted with DCM (2×100 mL). The combined organic layer is washed with water (2×50 mL) and saturated brine (50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude material is purified by silica gel chromatography, eluting with hexane:ethyl acetate (1:1) to give the title compound as a light yellow oil (9.2 g, 87.03%). ESI/MS m/z 174.1 (M+H)+.

Workup

  1. extractionextracted with DCM (2×100 mL)
  2. washThe combined organic layer is washed with water (2×50 mL) and saturated brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure
  5. customThe crude material is purified by silica gel chromatography
  6. washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-57f0900346ad416e995ef84474d8f22c
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

Loading…