Asparagusic acid → HCID 18358007, compound

HRID 428306Notes

Reaction equation

HRID 428306 reaction equation
[S:1]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3][S:2]1.Cl.[CH3:10][O:11][C:12](=[O:16])[CH2:13][CH2:14][NH2:15].P(C#N)(OCC)(OCC)=O>CN(C)C=O.O1CCCC1>[S:1]1[CH2:5][CH:4]([C:6]([NH:15][CH2:14][CH2:13][C:12]([O:11][CH3:10])=[O:16])=[O:8])[CH2:3][S:2]1

Participants

6

Reactant 3

HCID 16682Asparagusic acidHCID 76257Diethyl cyanophosphonateHCID 2734767Methyl 3-aminopropanoate hydrochloride

Product 1

HCID 18358007HCID 18358007, compoundYield 9.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out as described in Example 97, but using 5 ml of a solution of 3.3 mmol of 1,2-dithiolane-4-carboxylic acid (prepared as described in Example 96) in anhydrous dimethylformamide, 5 ml of anhydrous tetrahydrofuran, 1.01 ml of torethylamine, 502 mg of β-alanine methyl ester hydrochloride and 0.55 ml of diethyl cyanophosphate. The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the eluent. The solvent was removed from the eluate solution by evaporation under reduced pressure, and the residue was recrystallized from a 2:2 by volume mixture of ethyl acetate and hexane, to obtain 73 mg of the title compound as pale yellow crystals having an Rf value of 0.41 (silica gel thin layer chromatography; using a 2:1 by volume mixture of ethyl acetate and hexane as developing solvent).

Workup

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  7. additionby volume mixture of ethyl acetate and hexane as the eluent
  8. customThe solvent was removed from the eluate solution by evaporation under reduced pressure
  9. customthe residue was recrystallized from a 2:2 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-68adbd173e544803b3b798faaeab5885
Source dataset
uspto-grants-2001_11
Patent number
US06313164B1

Reaction notes

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