Triethylamine → 2-(Dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionic acid

HRID 466226Notes

Reaction equation

HRID 466226 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8](=O)[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.[CH3:19][O:20][P:21]([CH2:25][NH2:26])(=[O:24])[O:22][CH3:23].C(N(CC)CC)C.C([BH3-])#N.[Na+]>C1COCC1.CCO.C1COCC1>[CH3:19][O:20][P:21]([CH2:25][NH:26][CH:8]([CH2:7][C:4]1[CH:5]=[CH:6][C:1]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:2][CH:3]=1)[C:9]([OH:11])=[O:10])([O:22][CH3:23])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 13310504Dimethyl (aminomethyl)phosphonateHCID 139824372-Oxo-3-(4-phenylphenyl)propanoic acid

Product 1

HCID 538116872-(Dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21873804Tetrahydrofuran ethanolSolvent2×

Procedure

To a stirred suspension of 4-biphenylyl-pyruvic acid in anhydrous THF-EtOH (50 mL, 9:1) is added aminomethylphosphonic acid dimethyl ester (520 mg, 3.7 mmol) in THF-EtOH (5 mL, 9:1). The pH is then adjusted with triethylamine to 6.6. After 20 minutes, sodium cyanoborohydride (100 mg, 1.6 mmol) in THF (2.5 mL) is added over 30 minutes. The solution is stirred for 18 hours and then concentrated. Ether (20 mL) is added and the mixture is cooled and treated with 1N HCl (7 mL). After stirring at room temperature for 30 minutes, the solid is filtered off and washed with ether and water to yield 2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionic acid as a waxy solid.

Workup

  1. concentrationconcentrated
  2. additionEther (20 mL) is added
  3. temperaturethe mixture is cooled
  4. additiontreated with 1N HCl (7 mL)
  5. stirringAfter stirring at room temperature for 30 minutes
  6. filtrationthe solid is filtered off
  7. washwashed with ether and water

Sources & evidence

ORD record
ord-88519e83c63b408b8575ff0238645112
Source dataset
uspto-grants-1992_10
Patent number
US05155100

Reaction notes

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