N,O-bis(trimethylsilyl)acetamide → tert-Butyl {4-[(2R,3R)-3-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate

HRID 603917Notes

Reaction equation

HRID 603917 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][C@@H:20]([C:45](=[O:58])N4[C@@H](C5C=CC=CC=5)COC4=O)[C@@H:21]([C:30]4[CH:44]=[CH:43][C:33]([O:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:32][CH:31]=4)[NH:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][C@H:20]4[C:45](=[O:58])[N:22]([C:23]5[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=5)[C@@H:21]4[C:30]4[CH:44]=[CH:43][C:33]([O:34][CH2:35][C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])=[CH:32][CH:31]=4)[O:11][CH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][O:15]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 86643074tert-Butyl (4-{(1R,2R)-2-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-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 86643075tert-Butyl {4-[(2R,3R)-3-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-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-{(1R,2R)-2-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-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 (Method 15) (22.30 g, 27.4 mmol) was dissolved in dry toluene (800 mL) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 20.1 mL, 82.1 mmol) was added and the mixture was stirred at 90° C. for one hour. The mixture was then given 45° C. and tetrabutylammonium fluoride trihydrate (TBAF, cat., 1 g) was added and the mixture was stirred at 45° C. for 1 hour. The mixture was then concentrated under reduced pressure and purified by flash-chromatography (heptane:EtOAc 5:1). This afforded 10.0 g (56%) of the title compound as a white solid.

Workup

  1. customwas then given 45° C.
  2. stirringthe mixture was stirred at 45° C. for 1 hour
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. custompurified by flash-chromatography (heptane:EtOAc 5:1)

Sources & evidence

ORD record
ord-003246a37a55425494ec5673ab48dc6c
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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