Reaction #632040

Reaction equation

3-aminopropylmethylphosphinic acid

compound ( 17 )

[(1-Isobutanoyloxyethoxy)carbonyloxy] Succinimide

→

title compound ( 111 )

3-{[1-Isobutanoyloxyethoxy]carbonylamino}propyl Methylphosphinic Acid

Solvents

acetonitrile

water

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Otherthe residue was purified by preparative HPLC

Procedure

A solution of 3-aminopropylmethylphosphinic acid (137 mg, 1 mmol) and compound (17) (301 mg, 1 mmol) in acetonitrile (5 mL) and water (0.5 mL) was stirred at ambient temperature for 16 h. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to afford the title compound (111) as a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.69 (br, 1H), 6.77 (q, 1H, J=5.2 Hz), 3.27 (t, 2H, J=6 Hz), 2.53 (m, 1H), 1.83-1.73 (m, 4H), 1.45 (m, 6H), 1.15 (d, 6H, J=7.2 Hz). MS (ESI) m/z 296.1 (M+H)+, 294.1 (M−H)−.

Source