Pyridine → (3aR,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione

HRID 1715788Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715788
[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.N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)(=O)C>C(Cl)(Cl)Cl>[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

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 11360281(4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid

Produkt 1

HCID 86596559(3aR,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dioneAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

In 160 ml of chloroform was dissolved 20 g of (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid, 6.2 g of pyridine was added to the solution, and under ice-cooling, 40 ml of a chloroform solution containing 12.7 g of dicyclohexylcarbodiimide was added to the mixture at 15° C. or lower. The mixture was stirred at room temperature for 1 hour, ethyl acetate was added to the reaction mixture and the resulting mixture was filtered. The filtrate was washed successively with 2M hydrochloric acid, water, a saturated sodium bicarbonate solution, and saturated brine. The organic layer was dried and then concentrated. The residue was recrystallized from ethyl acetate to give 8.0 g of (3aR,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione.

Aufarbeitung

  1. additionwas added to the solution
  2. temperatureunder ice-cooling
  3. additionwas added to the mixture at 15° C.
  4. filtrationthe resulting mixture was filtered
  5. washThe filtrate was washed successively with 2M hydrochloric acid, water
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-002dd8c42b904dc88facc0a1fe649583
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799929B2

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