Hydrochloric Acid → HCID 21849258, compound

HRID 617833Notes

Reaction equation

HRID 617833 reaction equation
C([NH:4][C:5]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH2:8][OH:9])[CH2:6][OH:7])(=O)C.[OH-].[Na+].Cl>CO>[NH2:4][C:5]([CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([CH2:8][OH:9])[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21849144HCID 21849144, compound

Product 1

HCID 21849258HCID 21849258, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetamido-2-(3-phenylpropyl)-1,3-propanediol (600 mg) was dissolved in 25 ml of methanol and 11.9 ml of a 1 N aqueous sodium hydroxide solution was added thereto. The mixture was refluxed under heating for 6 hours. The mixture was poured into 30 ml of ice water and neutralized with dilute hydrochloric acid. The solvent was distilled away. Chloroform was added to the residue for extraction and the chloroform layer was washed and dried. The solvent was distilled away and the residue was purified by column chromatography (chloroform:methanol=9:1-4:1) to give 250 mg of 2-amino-2-(3-phenylpropyl)-1,3-propanediol as a pale yellow, oily substance.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 6 hours
  3. distillationThe solvent was distilled away
  4. additionChloroform was added to the residue for extraction
  5. washthe chloroform layer was washed
  6. customdried
  7. distillationThe solvent was distilled away
  8. customthe residue was purified by column chromatography (chloroform:methanol=9:1-4:1)

Sources & evidence

ORD record
ord-f5860eccb9c049b5b8a47d5552b5b865
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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