Sodium Hydroxide → 1-Oleoyl-lyso-phosphatidic acid

HRID 1530861Notes

Reaction equation

HRID 1530861 reaction equation
[Si]([O:18][CH:19]([CH2:41][O:42][P:43]([OH:46])([OH:45])=[O:44])[CH2:20][O:21][C:22](=[O:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+]>ClCCl>[OH:18][CH:19]([CH2:41][O:42][P:43]([OH:45])([OH:46])=[O:44])[CH2:20][O:21][C:22](=[O:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69746178HCID 69746178, compound

Product 1

HCID 54971521-Oleoyl-lyso-phosphatidic acidYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 (1 mmol) is dissolved in 10 ml of dichloromethane, and 25 ml of a 1% methanolic NaOH solution is added. This is concentrated after 20 hours at room temperature, and the residue is acidified with 1N HCl. The mixture is extracted with ethyl acetate. The combined organic phases are washed with 20 ml of H2O and dried over MgSO4, filtrated and concentrated. The residue is treated with methanol. Yield: 78% of colorless crystals.

Workup

  1. concentrationThis is concentrated after 20 hours at room temperature
  2. extractionThe mixture is extracted with ethyl acetate
  3. washThe combined organic phases are washed with 20 ml of H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. additionThe residue is treated with methanol

Sources & evidence

ORD record
ord-188b3d19ca2a4b939395f86a4069e1ff
Source dataset
uspto-grants-2001_03
Patent number
US06197759B1

Reaction notes

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