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

HRID 254096Notes

Reaction equation

HRID 254096 reaction equation
[CH3:1][C:2]1([CH3:56])[CH2:7][O:6][C:5]([CH2:15][S:16][C@@H:17]([C:42](=[O:55])N2[C@@H](C3C=CC=CC=3)COC2=O)[C@H:18]([C:27]2[CH:41]=[CH:40][C:30]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:29][CH:28]=2)[NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[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>[CH3:56][C:2]1([CH3:1])[CH2:7][O:6][C:5]([CH2:15][S:16][C@H:17]2[C:42](=[O:55])[N:19]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[C@@H:18]2[C:27]2[CH:41]=[CH:40][C:30]([O:31][CH2:32][C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])=[CH:29][CH:28]=2)([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 86619092tert-Butyl (4-{(1S,2R)-2-({[5,5-dimethyl-2-(4-methylphenyl)-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 86619093tert-Butyl {4-[(2R,3R)-3-({[5,5-dimethyl-2-(4-methylphenyl)-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-(4-methylphenyl)-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 (2.55 g, 3.25 mmol) was dissolved in dry toluene (250 ml) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 2.38 ml, 9.75 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, 0.25 g) was added and the mixture was stirred at 45° C. for one hour. The mixture was concentrated under reduced pressure and purified by flash-chromatography (hexane:EtOAc 6:1). This afforded 1.06 g (52%) of the title compound as a white solid. 1H-NMR (CDCl3, 200 MHz): δ 0.6 (s, 3H), 1.3 (s, 3H), 1.5 (s, 9H), 2.4 (s, 3H), 3.0-3.2 (m, 2H), 3.3-3.5 (m, 4H), 3.9 (d, 1H), 4.5 (s, 2H), 4.8 (d, 1H), 6.8-7.0 (m, 6H), 7.1-7.4 (m, 6H).

Workup

  1. temperatureThe mixture was cooled to 45° C.
  2. stirringthe mixture was stirred at 45° C. for one hour
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified by flash-chromatography (hexane:EtOAc 6:1)

Sources & evidence

ORD record
ord-a704e6465ce6459a928c2840d3a9794c
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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