Hydrochloric Acid → HCID 73848576, compound

HRID 1451600Notes

Reaction equation

HRID 1451600 reaction equation
C([NH:4][C:5]([CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:11][O:12]C(=O)C)[CH2:6][O:7]C(=O)C)(=O)C.[OH-].[Na+].[ClH:32]>CO>[ClH:32].[NH2:4][C:5]([CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:6][OH:7])[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54102978HCID 54102978, compound

Product 1

HCID 73848576HCID 73848576, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Acetamido-1,3-diacetoxy-2-(4-tetradecenyl)propane (450 mg) was dissolved in 27 ml of methanol and 9 ml of a 1N aqueous sodium hydroxide solution was added thereto. The mixture was refluxed under a nitrogen atmosphere for 8 hours. The reaction mixture was neutralized with hydrochloric acid and concentrated. Water was added to the concentrate and the mixture was subjected to chromatography using Sep-Pak(C18) (trade mark) and elution with methanol. The methanol eluate was concentrated to give 332 mg of pale yellow, oily 2-amino-2-(4-tetradecenyl)1,3-propanediol hydrochloride.

Workup

  1. temperatureThe mixture was refluxed under a nitrogen atmosphere for 8 hours
  2. concentrationconcentrated
  3. additionWater was added to the
  4. concentrationconcentrate
  5. washSep-Pak(C18) (trade mark) and elution with methanol
  6. concentrationThe methanol eluate was concentrated

Sources & evidence

ORD record
ord-e2a21cd054084eb0a8203c01eef3ba6f
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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