Dimethyl Sulfoxide → 4-[(1R,7aS)-1-Methyl-3,7-dioxo-hexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][C@@H:12]1[C@@H:19]2[N:15]([C:16](=[O:31])[N:17]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=3[CH3:30])[C@H:18]2[CH3:20])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:20][C@H:18]1[N:17]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=2[CH3:30])[C:16](=[O:31])[N:15]2[CH2:14][CH2:13][C:12](=[O:11])[C@H:19]12Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of DMSO (20 μL) in CH2Cl2 (1 mL) at −78° C. was added oxalyl chloride (1.0 M in CH2Cl2, 131 μL). This mixture was stirred at −78° C. for 30 min. and then a solution of 61K in CH2Cl2 (20 mg in 1 mL). The reaction was stirred at −78° C. for 1 h and then i-Pr2NEt (100 μL) was added and the reaction was allowed to warm to rt over 1 h. The reaction was extracted with EtOAc and washed twice with 1N HCl and once with saturated NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica gel, 40% EtOAc/CH2Cl2) provided the title compound (18 mg): MS (ES) m/z 304.42 [M+H]+
Workup
- stirringThe reaction was stirred at −78° C. for 1 h
- temperatureto warm to rt over 1 h
- extractionThe reaction was extracted with EtOAc
- washwashed twice with 1N HCl and once with saturated NaHCO3
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash chromatography (silica gel, 40% EtOAc/CH2Cl2)
Sources & evidence
- ORD record
- ord-6990011de6cc4b63afdfcda68ef903e1
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405234B2
Reaction notes
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