Water → HCID 86604368, compound
Reaction equation
[CH3:1]N(C)C=O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[NH:17][CH:18]=[CH:19][N:20]=2)=[CH:11][CH:10]=1)([O-:8])=[O:7].[H-].[Na+].O.[C:24]([O:27][CH2:28][CH3:29])(=O)C>>[CH3:1][C@@:28]1([CH2:29][N:20]2[CH:19]=[CH:18][N:17]=[C:16]2[S:15][C:12]2[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=2)[CH2:24][O:27]1Participants
Procedure
To N,N-dimethylformamide (5 ml) solution of 2-(4-nitrophenylthio)imidazole (500 mg) was added sodium hydride (90 mg) at 0° C., then reaction mixture was stirred at a room temperature for 30 minutes. After being cooled again the reaction mixture to 0° C., 2-methyl-2-oxiranylmethyl(S)-4-nitrobenzenesulfonate (618 mg) was added and stirred at a room temperature for 3.5 hours. Water and ethyl acetate were added to the reaction mixture, the organic layer was taken by separation. The ethyl acetate layer was washed with water and an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate. The residue obtained by removal of the solvent by distillation was purified by use of a silica gel column chromatography (eluent: dichlormethane/ethyl acetate=17/3), there was obtained (R)-1-(2-methyl-2-oxiranylmethyl)-2-(4-nitrophenylthio)imidazole (604 mg, yield: 91%) as yellow oily product.
Workup
- customreaction mixture
- temperatureAfter being cooled again the reaction mixture to 0° C.
- stirringstirred at a room temperature for 3.5 hours
- customthe organic layer was taken by separation
- washThe ethyl acetate layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customThe residue obtained by removal of the solvent by distillation
- customwas purified by use of a silica gel column chromatography (eluent: dichlormethane/ethyl acetate=17/3)
Sources & evidence
- ORD record
- ord-c87ae22865f14714805eb6542287c51e
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129544B2
Reaction notes
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