Reaktion #50057

ord-6b9ca4e7019243788b61798a3c6a6d67

Reaktionsgleichung

[Li+].[OH-]
lithium hydroxide
CCOP(=O)(CC1CCCCC1)C[C@@H](O)CNC(C)c1cccc(C#N)c1
3-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester
O=P(O)(O)O
phosphoric acid
→
CC(NC[C@H](O)CP(=O)([O-])CC1CCCCC1)c1cccc(C(=O)O)c1.[Li+]
lithium 3-{N-[1-(3-carboxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinate

Edukte

[Li+].[OH-]
lithium hydroxide
CCOP(=O)(CC1CCCCC1)C[C@@H](O)CNC(C)c1cccc(C#N)c1
3-{N-[1-(3-cyanophenyl)ethyl]amino}-2(S)-hydroxy-propyl(cyclohexylmethyl)phosphinic acid ethyl ester
O=P(O)(O)O
phosphoric acid

Reagenzien

Keine

Lösungsmittel

O
water
CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe batch is heated
  2. 2
    Temperaturunder reflux for 24 hours
  3. 3
    SonstigeThe solvent is removed
  4. 4
    Filtrationfiltered
  5. 5
    SonstigeRemoval of the solvent and crystallisation from ethanol/acetone

Vorschrift

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°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05424441uspto-grants-1995_06