Lithium Hydroxide → HCID 67682372, compound

HRID 1492974Notes

Reaction equation

HRID 1492974 reaction equation
[OH-].[Li+].C([O:5][P:6]([CH2:15][C@@H:16]([OH:33])[CH2:17][NH:18][C@H:19]([C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1)[CH3:20])([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])C>O>[CH3:32][O:31][C:23]1[CH:22]=[C:21]([C@@H:19]([NH:18][CH2:17][C@H:16]([OH:33])[CH2:15][P:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:5])[OH:7])[CH3:20])[CH:26]=[C:25]([O:27][CH3:28])[C:24]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67682363HCID 67682363, compound

Product 1

HCID 67682372HCID 67682372, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

10 ml of water and 0.24 g of lithium hydroxide are added to a solution of 2.05 g of 3-{N-[1(S)-(3,4,5-trimethoxyphenyl)ethyl]amino}-2(S)-hydroxy-propyl(benzyl)-phosphinic acid ethyl ester in 4 ml of water and the mixture is heated at reflux overnight. The then clear solution is cooled to room temperature, adjusted to pH 7 with phsophoric acid and concentrated to dryness by evaporation under reduced pressure. The evaporation residue is made into a slurry in hot methanol and filtered. After concentration of the filtrate by evaporation there remains a foam which, after crystallisation from isopropanol, yields 3-{N-[1(S)-(3,4,5-trimethoxyphenyl)ethyl]amino}-2(S)-hydroxypropyl-(benzyl)-phosphinic acid having a melting point of 204°-206°, [α]20D =-35.2°±1.2° (c=0.812 in methanol).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated to dryness by evaporation under reduced pressure
  4. filtrationfiltered
  5. customAfter concentration of the filtrate by evaporation
  6. customafter crystallisation from isopropanol

Sources & evidence

ORD record
ord-2ee3763ba92e4feea0c5fc9351d0a53f
Source dataset
uspto-grants-1994_12
Patent number
US05376684

Reaction notes

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