Triethylamine → 3-[(6R,7S)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl]imidazolidine-2,4-dione monohydrochloride
Reaction equation
[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(N(CC)CC)C.[N:31]([CH2:34][C:35](OCC)=[O:36])=[C:32]=[O:33]>C1COCC1.C(OCC)(=O)C>[ClH:15].[Cl:16][C:11]1[CH:10]=[C:9]([C@@H:8]2[O:7][CH2:6][CH2:5][NH:4][CH2:3][C@H:2]2[N:1]2[C:35](=[O:36])[CH2:34][NH:31][C:32]2=[O:33])[CH:14]=[CH:13][C:12]=1[Cl:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (100 mg) in THF (3 mL) were added triethylamine (0.058 ml) and ethyl isocyanatoacetate (0.047 mL) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, 2.0 M hydrogen chloride-ethanol solution (8 mL) was added to the obtained residue at room temperature, and the mixture was stirred at 80° C. for 3 weeks. The residue obtained by concentration under reduced pressure was washed with diethyl ether to give the title compound (89 mg).
Workup
- washThe diluted solution was washed with distilled water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure, 2.0 M hydrogen chloride-ethanol solution (8 mL)
- additionwas added to the obtained residue at room temperature
- stirringthe mixture was stirred at 80° C. for 3 weeks
- customThe residue obtained by concentration under reduced pressure
- washwas washed with diethyl ether
Sources & evidence
- ORD record
- ord-4ac44ee4f40b4853a598afe7c3d4cd19
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722662B2
Reaction notes
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