Beta-Propiolactone → N-Phenyl-beta-alanine

HRID 1662148Notes

Reaction equation

HRID 1662148 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=[O:12])[O:11][CH2:10][CH2:9]1>C(#N)C>[C:2]1([NH:1][CH2:10][CH2:9][C:8]([OH:12])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2365Beta-PropiolactoneHCID 6115Aniline

Product 1

HCID 244082N-Phenyl-beta-alanine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Aniline (9.11 mL, 100 mmol) was dissolved in acetonitrile (100 mL) and heated to reflux while β-propiolactone (Sigma, 6.29 mL, 100 mmol) in acetonitrile (20 mL) was added dropwise for 30 minutes. The mixture was refluxed for 3 hours and then stirred overnight at ambient temperature. The mixture was concentrate under reduced pressure, and chromatographed on silica gel eluting with 40-to-100% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 2.69 (t, J=6.27 Hz, 2H), 3.48 (t, J=6.44 Hz, 2H), 6.66 (dd, J=8.81, 1.02 Hz, 2H), 6.75 (t, J=7.46 Hz, 1H), 7.20 (dd, J=8.65, 7.29 Hz, 2H). MS (DCI) m/z 166.05 (M+H)+.

Workup

  1. temperatureheated
  2. additionwas added dropwise for 30 minutes
  3. temperatureThe mixture was refluxed for 3 hours
  4. concentrationThe mixture was concentrate under reduced pressure
  5. customchromatographed on silica gel eluting with 40-to-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1811f04a5e2141d3adde078940ae31c1
Source dataset
uspto-grants-2011_10
Patent number
US08030504B2

Reaction notes

Loading…