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

HRID 1715787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715787
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-9b192616aa6c4defa66042279532ded5
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799929B2

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