Ethyl Acetate → (3AS-cis)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-D]imidazole-2,4-dione

HRID 2057124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057124
Cl.[CH2:2]([NH:9][C@@H:10]([C@@H:14]1[CH2:18][S:17][C:16](=[O:19])[N:15]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11](=[O:13])N)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:20]([N:15]1[C@H:14]2[CH2:18][S:17][C:11](=[O:13])[C@H:10]2[N:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:16]1=[O:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 8857Ethyl AcetateHCID 68508877(4R)-4-[(1S)-1-(N-benzylamino)-1-carbamoylmethyl]-3-benzylthiazolidin-2-one hydrochloride

Produkt 1

HCID 119817(3AS-cis)-1,3-Dibenzyltetrahydro-1H-thieno[3,4-D]imidazole-2,4-dioneAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In 10 ml of N,N-dimethylformamide was dissolved 0.541 g of (4R)-4-[(1S)-1-(N-benzylamino)-1-carbamoylmethyl]-3-benzylthiazolidin-2-one hydrochloride, the solution was stirred under nitrogen atmosphere at 100° C. for 3 hours. Ethyl acetate was added to the reaction mixture, and the resulting mixture was washed with water, and saturated brine, dried and concentrated. The residue was crystallized from hexane to give 342 mg of (3aS,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione as colorless crystal.

Aufarbeitung

  1. washthe resulting mixture was washed with water, and saturated brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-ea03eb1fa36f4a64805a122612f41a60
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335778B2

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