Tetrabutylammonium Fluoride → tert-Butyl (4-{(2R,3R)-1-(4-chlorophenyl)-3-[(4-methoxybenzyl)thio]-4-oxoazetidin-2-yl}phenoxy)acetate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]([C:35]2[CH:49]=[CH:48][C:38]([O:39][CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:37][CH:36]=2)[CH:10]([S:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:11](=[O:24])N2[C@@H](C3C=CC=CC=3)COC2=O)=[CH:4][CH:3]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:24])[C@H:10]([S:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C@H:9]2[C:35]2[CH:36]=[CH:37][C:38]([O:39][CH2:40][C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])=[CH:48][CH:49]=2)=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
tert-Butyl (4-{(1R)-1-[(4-chlorophenyl)amino]-2-[(4-methoxybenzyl)thio]-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate (Method 25) (2.3 g, 3.3 mmol) was dissolved in dry toluene (250 mL) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 2.4 mL, 9.8 mmol) was added and the mixture was stirred at 90° C. for one hour. The mixture was then given 45° C. and tetrabutylammonium fluoride (TBAF, 0.2 g) was added. The mixture was stirred at 45° C. for 2 hours. After cooling, the mixture was concentrated under reduced pressure and purified by flash-chromatography (Heptane:EtOAc 4:1). This afforded the title compound.
Workup
- customwas then given 45° C.
- stirringThe mixture was stirred at 45° C. for 2 hours
- temperatureAfter cooling
- concentrationthe mixture was concentrated under reduced pressure
- custompurified by flash-chromatography (Heptane:EtOAc 4:1)
Sources & evidence
- ORD record
- ord-391dc019628a43c3ab4cf398e2018c36
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906502B2
Reaction notes
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