3-Aminopropyl-cyclohexylmethylphosphinic acid → HCID 68455686, compound

HRID 2353221Notes

Reaction equation

HRID 2353221 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:7])[OH:6].C(=O)(O)[O-].[Na+].[C:20]([O:25][CH:26]([O:28][C:29](OC1CC(=O)NC1=O)=[O:30])[CH3:27])(=[O:24])[CH:21]([CH3:23])[CH3:22]>O.C(#N)C.C(OCC)C>[C:20]([O:25][CH:26]([O:28][C:29]([NH:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:6])[OH:7])=[O:30])[CH3:27])(=[O:24])[CH:21]([CH3:23])[CH3:22]

Participants

7

Reactant 3

HCID 1300223-Aminopropyl-cyclohexylmethylphosphinic acidHCID 516892Sodium BicarbonateHCID 66743414[(1-Isobutanoyloxyethoxy)carbonyloxy]succinimide

Product 1

HCID 68455686HCID 68455686, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-aminopropyl(cyclohexylmethyl)phosphinic acid (10 mmol) and sodium bicarbonate (20 mmol) in water (40 mL) is added a solution of compound (17) (10 mmol) in acetonitrile (20 mL) over 1 min. The reaction is stirred at ambient temperature for 16 h. The reaction mixture is diluted with diethyl ether (100 mL) and washed with 0.1 M aqueous potassium bisulfate (3×100 mL). The organic phase is separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound (91) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-4f09ceadacef43658f72ac3eab3bcf21
Source dataset
uspto-grants-2010_07
Patent number
US07749985B2

Reaction notes

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