(3-Aminopropyl)(n-butyl)phosphinic acid → HCID 86620831, compound

HRID 2353219Notes

Reaction equation

HRID 2353219 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:8][CH2:9][CH2:10][CH3:11])(=[O:7])[OH:6].C(=O)(O)[O-].[Na+].[C:17]([O:22][CH:23]([O:25][C:26](OC1CC(=O)NC1=O)=[O:27])[CH3:24])(=[O:21])[CH:18]([CH3:20])[CH3:19]>O.C(#N)C.C(OC(=O)C)C>[C:17]([O:22][CH:23]([O:25][C:26]([NH:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:8][CH2:9][CH2:10][CH3:11])(=[O:6])[OH:7])=[O:27])[CH3:24])(=[O:21])[CH:18]([CH3:20])[CH3:19]

Participants

7

Reactant 3

HCID 130021(3-Aminopropyl)(n-butyl)phosphinic acidHCID 516892Sodium BicarbonateHCID 66743414[(1-Isobutanoyloxyethoxy)carbonyloxy]succinimide

Product 1

HCID 86620831HCID 86620831, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-aminopropyl(n-butyl)phosphinic acid (10 mmol) and sodium bicarbonate (20 mmol) in water (40 mL) was added a solution of compound (17) (10 mmol) in acetonitrile (20 mL) over 1 min. The reaction was stirred at ambient temperature for 16 h. The reaction mixture was diluted with ethylacetate (100 mL) and washed with 0.1 M aqueous potassium bisulfate (3×100 μL). The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound (31) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 6.78 (q, J=8 Hz, 1H), 3.49 (s, 1H), 3.28 (t, J=6.4 Hz, 2H), 2.51-2.55 (m, 1H), 1.80-1.84 (m, 2H), 1.65-1.75 (m, 3H), 1.55-1.58 (m, 2H), 1.39-1.48 (m, 4H), 1.17 (d, J=8.4 Hz, 9H), 0.93 (t, J=7.2 Hz, 3H). Phosphorus (162 MHz, CDCl3) δ0.31. MS (ESI) m/z 338 (M+H)+.

Workup

  1. washwashed with 0.1 M aqueous potassium bisulfate (3×100 μL)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7f4ecbd57354b429f0296fc91ceaa4c
Source dataset
uspto-grants-2010_07
Patent number
US07749985B2

Reaction notes

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