Tetrabutylammonium Fluoride → tert-Butyl {4-[(2R,3R)-3-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate

HRID 254086Notes

Reaction equation

HRID 254086 reaction equation
[CH3:1][C:2]1([CH3:55])[CH2:7][O:6][C:5]([CH2:14][S:15][C@@H:16]([C:41](=[O:54])N2[C@@H](C3C=CC=CC=3)COC2=O)[C@H:17]([C:26]2[CH:40]=[CH:39][C:29]([O:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:28][CH:27]=2)[NH:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][CH2:3]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>[CH3:55][C:2]1([CH3:1])[CH2:7][O:6][C:5]([CH2:14][S:15][C@H:16]2[C:41](=[O:54])[N:18]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[C@@H:17]2[C:26]2[CH:40]=[CH:39][C:29]([O:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:28][CH:27]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 86619086tert-Butyl (4-{(1S,2R)-2-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-1-[(4-fluorophenyl)amino]-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate

Product 1

HCID 86641029tert-Butyl {4-[(2R,3R)-3-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

tert-Butyl (4-{(1S,2R)-2-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-1-[(4-fluorophenyl)amino]-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate (2.6 g, 3.4 mmol) was dissolved in dry toluene (250 ml) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 2.5 ml, 10.3 mmol) was added and the mixture was stirred at 90° C. for one hour. The mixture was cooled to 45° C. and tetrabutylammonium fluoride (TBAF, cat., 0.5 g) was added. The mixture was stirred at 45° C. for two hours. The mixture was concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc 7:1). This afforded 0.65 g (31%) of the title compound as a yellow solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.2 (s, 3H), 1.5 (s, 9H), 2.9-3.1 (q, broad, 2H), 3.4 (q, 4H), 4.0 (s, 1H), 4.5 (s, 2H), 4.8 (s, 1H), 6.9-7.0 (m, 4H), 7.2-7.3 (m, 5H), 4.3-4.4 (m, 4H).

Workup

  1. temperatureThe mixture was cooled to 45° C.
  2. stirringThe mixture was stirred at 45° C. for two hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified by flash-chromatography (hexane:EtOAc 7:1)

Sources & evidence

ORD record
ord-b9c4d57c64844f2c81e314efad560602
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

Loading…