Ethyl Acetate → 1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

HRID 2057124Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

washthe resulting mixture was washed with water, and saturated brine
customdried
concentrationconcentrated
customThe residue was crystallized from hexane

Sources & evidence

ORD record: ord-ea03eb1fa36f4a64805a122612f41a60
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335778B2

Reaction notes

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