Dimethyl Sulfoxide → HCID 20081836, compound
Reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.CS(C)=O.[CH:18]([C:21]1[C:26]([CH2:27][OH:28])=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:24]([CH2:36][N:37]2CCOCC2)=[C:23]([CH:43](C)C)[N:22]=1)([CH3:20])[CH3:19].C(N(CC)CC)C>C(Cl)Cl>[C:36]([C:24]1[C:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)=[C:26]([CH:27]=[O:28])[C:21]([CH:18]([CH3:20])[CH3:19])=[N:22][C:23]=1[CH3:43])#[N:37]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
4.4 g (21 mmol) of trifluoroacetic anhydride in 15 ml of methylene chloride are added dropwise at -78° C. to 1.1 g (14 mmol) of DMSO in 8 ml of methylene chloride p.A. and the mixture is stirred for 10 minutes at -70° C. 2.1 g (7 mmol) of compound 2 from Example 143 are then added in 50 ml of methylene chloride, the mixture is stirred for 1 h at -70° C., 5.8 ml (42 mmol) of triethylamine are now added and the mixture is stirred for 4 h at room temperature. It is washed with saturated sodium chloride solution, concentrated, chromatographed over 100 g of silica gel (230-400 mesh, φ4 cm, petroleum ether/ethyl acetate 10:1) and recrystallized from ethyl acetate/petroleum ether.
Workup
- stirringthe mixture is stirred for 1 h at -70° C.
- stirringthe mixture is stirred for 4 h at room temperature
- washIt is washed with saturated sodium chloride solution
- concentrationconcentrated
- customchromatographed over 100 g of silica gel (230-400 mesh, φ4 cm, petroleum ether/ethyl acetate 10:1)
- customrecrystallized from ethyl acetate/petroleum ether
Sources & evidence
- ORD record
- ord-5dd1d4ce928843aaa866ead705861b5b
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401746
Reaction notes
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