Sodium Bicarbonate → 3-{[1-Isobutanoyloxyethoxy]carbonylamino}propyl Phosphonous Acid

HRID 544856Notes

Reaction equation

HRID 544856 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([OH:7])[OH:6].C(=O)(O)[O-].[Na+].[C:13]([O:18][CH:19]([O:21][C:22](OC1CC(=O)NC1=O)=[O:23])[CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15]>O.C(#N)C.C(OCC)C>[C:13]([O:18][CH:19]([O:21][C:22]([NH:1][CH2:2][CH2:3][CH2:4][P:5]([OH:7])[OH:6])=[O:23])[CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 99892683-Amino-propanephosphonousHCID 66743414[(1-Isobutanoyloxyethoxy)carbonyloxy]succinimide

Product 1

HCID 866051023-{[1-Isobutanoyloxyethoxy]carbonylamino}propyl Phosphonous Acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-aminopropylphosphonous 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 (31) 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-925f4afc929f45159f2e5845d12a826e
Source dataset
uspto-grants-2011_05
Patent number
US07935686B2

Reaction notes

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