Trifluoroacetic acid → 1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

HRID 1715784Notes

Reaction equation

HRID 1715784 reaction equation
[CH2:1]([N:8]1[C@@H:12]([CH2:13][SH:14])[C@H:11]([C:15](O)=[O:16])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](=[O:16])[C@H:11]2[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 11360281(4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid

Product 1

HCID 1198171,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dioneYield 74.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

To 240 ml of a chloroform solution containing 30 g of (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid, 22.7 g of pyridine and 2.6 ml of trifluoroacetic acid was added dropwise 60 ml of a chloroform solution containing 17.4 g of dicyclohexylcarbodiimide at 5° C. over 30 minutes. After the solution was refluxed for 5 hours, it was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate and concentrated, and after the procedure was repeated, 300 ml of ethyl acetate was added to the residue, and the mixture was stirred at 50° C. for 30 minutes. After cooling to 25° C., insoluble materials were filtered off. After the filtrate was concentrated, 85 ml of methanol was added to the concentrate and the mixture was dissolved under heating. After cooling the solution, precipitated crystal was collected by filtration, and washed with cold methanol. Precipitated crystal was dried by blowing air at 50° C. to give 21.3 g of (3aS,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione as colorless crystal.

Workup

  1. temperatureAfter the solution was refluxed for 5 hours
  2. concentrationit was concentrated under reduced pressure
  3. dissolutionThe concentrate was dissolved in ethyl acetate
  4. concentrationconcentrated
  5. addition300 ml of ethyl acetate was added to the residue
  6. temperatureAfter cooling to 25° C.
  7. filtrationinsoluble materials were filtered off
  8. concentrationAfter the filtrate was concentrated
  9. addition85 ml of methanol was added to the
  10. concentrationconcentrate
  11. dissolutionthe mixture was dissolved
  12. temperatureunder heating
  13. temperatureAfter cooling the solution
  14. customprecipitated crystal
  15. filtrationwas collected by filtration
  16. washwashed with cold methanol
  17. customPrecipitated crystal
  18. customwas dried
  19. customat 50° C.

Sources & evidence

ORD record
ord-6dfcc08c68cf49e1bd3b1ad019db3d5f
Source dataset
uspto-grants-2010_09
Patent number
US07799929B2

Reaction notes

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