1-Amino-2-propanol → Ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate

HRID 2200582Notes

Reaction equation

HRID 2200582 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].Cl[C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(Cl)Cl>[OH:5][CH:3]([CH3:4])[CH2:2][NH:1][C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 41-Amino-2-propanolHCID 20884Ethoxalyl chloride

Product 1

HCID 85994322Ethyl 2-(2-hydroxypropylamino)-2-oxo-acetateYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-aminopropan-2-ol (2 g, 26.6 mmol) and TEA (4.03 g, 39.9 mmol) in DCM (50 mL) was added ethyl 2-chloro-2-oxoacetate (4.36 g, 31.95 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 16 h. The mixture was diluted with DCM and extracted with brine. The organic layer was dried and concentrated to give a crude product which was purified by silica gel chromatography eluting with petroleum ether/ethyl acetate (2:1) to give ethyl 2-(2-hydroxypropylamino)-2-oxoacetate (2.19 g, 51% yield) as yellow syrup. LCMS retention time 0.348 min, LCMS MH+ 176.

Workup

  1. extractionextracted with brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified by silica gel chromatography
  6. washeluting with petroleum ether/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-d07e995c27354afc842bb1d47a299146
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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