Phosphoric Acid → HCID 67682372, compound

HRID 1440688Notes

Reaction equation

HRID 1440688 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.P(=O)(O)(O)O>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

5

Reactant 3

HCID 1004Phosphoric AcidHCID 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 phosphoric 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)-hydroxy-propyl-(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-af96d4369a574456b92dad3627acf607
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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