Water → HCID 18658105, compound

HRID 1440691Notes

Reaction equation

HRID 1440691 reaction equation
[OH-].[Li+].O.C([O:6][P:7]([CH2:15][C@@H:16]([OH:19])[CH2:17][NH2:18])([CH:9]1[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1)=[O:8])C.P(=O)(O)(O)O>C(O)C>[NH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][P:7]([CH:9]1[CH2:14][CH2:13][CH:12]=[CH:11][CH2:10]1)(=[O:6])[OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 3939Lithium HydroxideHCID 53777184HCID 53777184, compound

Product 1

HCID 18658105HCID 18658105, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.2 g of lithium hydroxide and 4 ml of water are added to a solution of 1.1 g of 3-amino-2(S)-hydroxy-propyl-(cyclohex-3-enyl)-phosphinic acid ethyl ester in 4 ml of ethanol. The mixture is heated to 60° and stirred for 20 hours. The mixture is then allowed to cool to room temperature, adjusted to pH 7 with aqueous phosphoric acid, concentrated to dryness by evaporation, taken up in methanol/water and filtered. After removal of the solvent there remains behind a foam which, after crystallisation from ethanol/methanol, yields 3-amino-2(S)-hydroxy-propyl-(cyclohex-3-enyl)-phosphinic acid in the form of white crystals having a melting point of 221°-225°.

Workup

  1. temperatureThe mixture is heated to 60°
  2. concentrationconcentrated to dryness by evaporation
  3. filtrationfiltered
  4. customAfter removal of the solvent
  5. customafter crystallisation from ethanol/methanol

Sources & evidence

ORD record
ord-3eabf05928c44a6e95630fb6a28d1e47
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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