Acetaldehyde → HCID 22012686, compound

HRID 1533174Notes

Reaction equation

HRID 1533174 reaction equation
[CH2:1]([OH:8])[CH2:2][C:3]#[C:4][CH2:5][C:6]#[CH:7].C([Mg]Br)C.[CH:13](=[O:15])C.[C:16](Cl)(=O)C1C=CC=CC=1.[Cl-].[NH4+].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO.N1C=CC=CC=1.O1CCCC1.C(OCCOCCOCC)C>[CH2:13]([OH:15])[CH2:7][C:6]#[C:5][CH2:4][C:3]#[C:2][CH:1]([OH:8])[CH3:16]

Participants

12

Reactant 7

HCID 177AcetaldehydeHCID 6101p-Toluenesulfonic acidHCID 7412Benzoyl chlorideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 105346313,6 heptadiynolHCID 178418443HCID 178418443, compound

Product 1

HCID 22012686HCID 22012686, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×HCID 8179Diethylene glycol diethyl etherSolvent

Procedure

More specifically, to chemically prepare the compounds of the invention, the C16-C24 fatty acids are prepared first, and isolated. The isolated fatty acid is then conjugated to the amino acid. The first step of the process produces a 1-ethoxyethyloxy-8-benzoyl-3,6-nonadiyne [I] by reacting ethoxyethyl ether of 3,6 heptadiynol in an anhydrous ethereal solvent, such as, for example, tetrahydrofuran with an organometallic base, such as, for example, ethylmagnesiumbromide in an anhydrous ethereal solvent, tetrahydrofuran, for example, at about 0° C. Approximately 1 ml of acetaldehyde, or any other aldehyde, is added to the mixture. The mixture is then treated with an anhydrous tertiary amine base, such as for example, pyridine, followed by benzoyl chloride to acylate the resulting alcohol. This mixture is stirred for approximately 1 hour and is then treated with a saturated ammonium chloride and extracted into a non-polar solvent, such as, for example, diethyl ether. The organic phase is separated, washed in brine and dried over anhydrous inorganic salt, such as, for example, MgSO4. For the purposes of this application, brine is defined as a saturated sodium chloride solution. The dried preparation containing I is reconstituted in an alcohol solvent, such as, for example, methanol and treated with an organic acid, such as for example, p-toluenesulfonic acid to remove the ethoxyethyl ether group. This is allowed to react until almost no starting materials remain. The mixture is treated with a mild inorganic base, such as for example, NaHCO3, and the solvent is removed in vacuo. The residue is taken up in a non-polar solvent, such as for example, diethyl ether and purified by liquid chromatography over silica gel to obtain 3,6-nonadiyne-1,8-diol, 8-benzoate. The solvent is removed in vacuo and the residue taken up in an alcoholic solvent, such as, for example, ethanol, containing quinoline and Lindlar catalyst and stirred at about room temperature until hydrogen uptake ceases. The product is isolated by liquid chromatography through celite and the solvent removed in vacuo. The residue is taken up in a non-polar solvent, such as, for example, diethyl ether, washed with dilute aqueous acid, such as, for example, 10% HCL, and dried over an anhydrous inorganic salt, such as, for example, MgSO4. The dried residue is taken up in methylene chloride and this contains compound II.

Workup

  1. customat about 0° C
  2. extractionextracted into a non-polar solvent
  3. customThe organic phase is separated
  4. washwashed in brine
  5. customdried over anhydrous inorganic salt
  6. customThe dried preparation
  7. additioncontaining I
  8. customto remove the ethoxyethyl ether group
  9. customto react until almost no starting materials
  10. customthe solvent is removed in vacuo
  11. custompurified by liquid chromatography over silica gel

Sources & evidence

ORD record
ord-9a8a0bad56ed4d409408b8be686c4055
Source dataset
uspto-grants-2001_03
Patent number
US06207712B1

Reaction notes

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