Phosphoric Acid → lithium 3-{N-[1-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinate

HRID 21779Notes

Reaction equation

HRID 21779 reaction equation
[OH-:1].[Li+:2].C([O:5][P:6]([CH2:15][C@@H:16]([OH:29])[CH2:17][NH:18][CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#N)[CH:22]=1)[CH3:20])([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])C.P(=O)(O)(O)[OH:31]>O.C(O)C>[C:27]([C:23]1[CH:22]=[C:21]([CH:19]([NH:18][CH2:17][C@H:16]([OH:29])[CH2:15][P:6]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)(=[O:7])[O-:5])[CH3:20])[CH:26]=[CH:25][CH:24]=1)([OH:31])=[O:1].[Li+:2]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 3939Lithium HydroxideHCID 15282288HCID 15282288, compound

Product 1

HCID 67565819lithium 3-{N-[1-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.4 g of lithium hydroxide in 10 ml of water is added to a solution of 3.0 g of 3-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester in 10 ml of ethanol and the batch is heated under reflux for 24 hours. It is cooled to 4° and neutralised with aqueous phosphoric acid. The solvent is removed and the residue is taken up in warm methanol and filtered. Removal of the solvent and crystallisation from ethanol/acetone gives lithium 3-{N-[1-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinate having a melting point of 160°-184°.

Workup

  1. temperaturethe batch is heated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent is removed
  4. filtrationfiltered
  5. customRemoval of the solvent and crystallisation from ethanol/acetone

Sources & evidence

ORD record
ord-6b9ca4e7019243788b61798a3c6a6d67
Source dataset
uspto-grants-1995_06
Patent number
US05424441

Reaction notes

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