2,6-Lutidine → HCID 86627641, compound
Reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.N1C(C)=CC=CC=1C.[F:24][C:25]([F:52])([F:51])[C:26]1[CH:27]=[C:28]([C@H:36]2[O:40][C:39](=[O:41])[N:38]([CH2:42][C:43]3[C:48](O)=[N:47][CH:46]=[CH:45][N:44]=3)[C@H:37]2[CH3:50])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:48]1[C:43]([CH2:42][N:38]2[C@@H:37]([CH3:50])[C@@H:36]([C:28]3[CH:29]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:31]=[C:26]([C:25]([F:52])([F:24])[F:51])[CH:27]=3)[O:40][C:39]2=[O:41])=[N:44][CH:45]=[CH:46][N:47]=1)(=[O:8])=[O:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a cold (−78° C.) mixture of trifluoromethanesulfonic anhydride (0.284 mL, 1.681 mmol), 2,6-lutidine (0.261 mL, 2.241 mmol) and CH2Cl2 (1 mL) was added (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-hydroxypyrazin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (472 mg, 1.120 mmol) in CH2Cl2 (1 mL). The resulting mixture was stirred at −78° C. for 30 min then the cold bath was switched to an ice bath. Reaction mixture was stirred cold (0° C.) for additional 2 h. Crude mixture was worked up with water/CH2Cl2/Na2SO4/filtration/concentration to afford an orange oil. This was purified by preparative TLC (silica gel) developed with a EtOAc (30% v/v)/hexanes mixture to give a yellow oil as the titled compound. LCMS calc.=553.04; found=554.02 (M+H)+.
Workup
- customthe cold bath was switched to an ice bath
- customReaction mixture
- stirringwas stirred cold (0° C.) for additional 2 h
- concentrationCrude mixture was worked up with water/CH2Cl2/Na2SO4/filtration/concentration
- customto afford an orange oil
- customThis was purified by preparative TLC (silica gel)
Sources & evidence
- ORD record
- ord-48197d0d15bb4135b9b16dbc1bb0160e
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910592B2
Reaction notes
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