(3-Aminopropyl)methylphosphinic acid → 3-{[1-Isobutanoyloxyethoxy]carbonylamino}propyl Methylphosphinic Acid

HRID 1726944Notes

Reaction equation

HRID 1726944 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH3:8])(=[O:7])[OH:6].[C:9]([O:14][CH:15]([O:17][C:18](OC1CC(=O)NC1=O)=[O:19])[CH3:16])(=[O:13])[CH:10]([CH3:12])[CH3:11]>C(#N)C.O>[C:9]([O:14][CH:15]([O:17][C:18]([NH:1][CH2:2][CH2:3][CH2:4][P:5]([CH3:8])(=[O:6])[OH:7])=[O:19])[CH3:16])(=[O:13])[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 5230(3-Aminopropyl)methylphosphinic acidHCID 66743414[(1-Isobutanoyloxyethoxy)carbonyloxy]succinimide

Product 1

HCID 115584183-{[1-Isobutanoyloxyethoxy]carbonylamino}propyl Methylphosphinic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

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)−.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-71d280a095524efaa4d5ec81142d7d93
Source dataset
uspto-grants-2009_02
Patent number
US07494985B2

Reaction notes

Loading…