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

HRID 544858Notes

Reaction equation

HRID 544858 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-1abb1872725648b6a0755d13c9519520
Source dataset
uspto-grants-2011_05
Patent number
US07935686B2

Reaction notes

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