Triethylamine → 2,2-Dimethyl-5-oxo-3-(2-oxo-1-pyrrolidineacetyl)-1-imidazolidineacetamide
Reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([OH:10])=O.C(N(CC)CC)C.ClC(OCCCC)=O.[CH3:26][C:27]1([CH3:37])[NH:31][CH2:30][C:29](=[O:32])[N:28]1[CH2:33][C:34]([NH2:36])=[O:35]>CN(C)C=O>[CH3:26][C:27]1([CH3:37])[N:31]([C:8](=[O:10])[CH2:7][N:3]2[CH2:4][CH2:5][CH2:6][C:2]2=[O:1])[CH2:30][C:29](=[O:32])[N:28]1[CH2:33][C:34]([NH2:36])=[O:35]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
An ice cold solution of 2-oxo-1-pyrrolidineacetic acid (1.45 g) and triethylamine (1.45 ml) in dimethylformamide (7 ml) was treated dropwise while stirring with butyl chloroformate (1.3 ml). After stirring at 0° C. for 45 minutes, 2,2-dimethyl-5-oxo-1-imidazolidineacetamide (1.75 g) was added at once and stirring was prolonged at room temperature overnight. After evaporation under reduced pressure, the residue was chromatographed on a silica gel column, eluting with dichloromethane/methanol 1:1. The selected fractions were collected and evaporated, the residue was taken up with ethyl acetate and the resulting solid was crystallized from ethanol, to give the title compound as a white powder, m.p. 225°-227° C., (decomp.).
Workup
- stirringstirring
- waitwas prolonged at room temperature overnight
- customAfter evaporation under reduced pressure
- customthe residue was chromatographed on a silica gel column
- washeluting with dichloromethane/methanol 1:1
- customThe selected fractions were collected
- customevaporated
- customthe resulting solid was crystallized from ethanol
Sources & evidence
- ORD record
- ord-8bd97c6e19a4404ca2ced4eba6826bdc
- Source dataset
- uspto-grants-1987_10
- Patent number
- US04703054
Reaction notes
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