Tetrahydrofuran → HCID 18357974, compound

HRID 849579Notes

Reaction equation

HRID 849579 reaction equation
O1CCCC1.Cl.[CH3:7][O:8][C:9](=[O:12])[CH2:10][NH2:11].[S:13]1[CH2:17][CH:16]([C:18](O)=[O:19])[CH2:15][S:14]1.P(C#N)(OCC)(OCC)=O>CN(C)C=O.C(N(CC)CC)C>[S:13]1[CH2:17][CH:16]([C:18]([NH:11][CH2:10][C:9]([O:8][CH3:7])=[O:12])=[O:19])[CH2:15][S:14]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 16682Asparagusic acidHCID 76257Diethyl cyanophosphonateHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 18357974HCID 18357974, compoundYield 7.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

5 ml of anhydrous tetrahydrofuran, 1.01 ml of triethylamine and 398 mg of glycine methyl ester hydrochloride were added to 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, and 0.55 ml of diethyl cyanophosphate was then added to the resulting mixture, whilst the ice-cooling, after which the mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction mixture was left to stand at room temperature overnight, after which the solvent was removed from the reaction mixture by evaporation under reduced pressure. Water was added to the residue, and the mixture 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 then removed from the eluate solution by evaporation under reduced pressure, and the residue was recrystallized from a 1:2 by volume mixture of ethyl acetate and hexane, to obtain 54 mg of the title compound as pale yellow crystals, melting at 73 to 75° C.

Workup

  1. temperaturecooling
  2. waitAt the end of this time, the reaction mixture was left
  3. waitto stand at room temperature overnight
  4. customafter which the solvent was removed from the reaction mixture by evaporation under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  10. additionby volume mixture of ethyl acetate and hexane as the eluent
  11. customThe solvent was then removed from the eluate solution by evaporation under reduced pressure
  12. customthe residue was recrystallized from a 1:2 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-ed59e03ac4774e97bd7050c0192557f1
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

Loading…