Potassium Hydroxide → Ethyl 2-(tert-butoxycarbonylaminooxy)propanoate

HRID 1959643Notes

Reaction equation

HRID 1959643 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[OH-].[K+].Br[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CCO>[C:5]([O:4][C:3]([NH:2][O:1][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:9])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 79040Ethyl 2-bromopropionateHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 58190590Ethyl 2-(tert-butoxycarbonylaminooxy)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of t-butyl hydroxycarbamate (530 mg, 3.98 mmol) and potassium hydroxide (223 mg, 3.98 mmol) in EtOH (10 mL) was added ethyl 2-bromopropanoate (600 mg, 3.31 mmol) slowly at rt. The reaction mixture was heated at reflux overnight. White precipitate was filtered off and the filtrate was concentrated. The resulting residue was dissolved in ether, washed with water and brine, and dried over Na2SO4. Solvent was evaporated to afford the title compound as a clear oil which was used in the next step without further purification (825 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ ppm 7.62 (s, 1H), 4.46 (q, 1H), 4.24 (q, 2H), 1.46 (d, 3H), 1.48 (s, 9H), 1.28 (t, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationWhite precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in ether
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. customSolvent was evaporated

Sources & evidence

ORD record
ord-5742fb8feb8142aaa78486ed6bfb7f70
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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