(Trifluoromethyl)trimethylsilane → HCID 69093936, compound

HRID 1396297Notes

Reaction equation

HRID 1396297 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([C@H:22]1[O:30][C@H:29]2[C@H:25]([N:26]=[C:27]([N:31]([CH2:39][CH:40]=[CH2:41])[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[S:28]2)[C@@H:24]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@@H:23]1[O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)(=[O:21])[CH3:20].[C:58]([Si](C)(C)C)([F:61])([F:60])[F:59]>C1COCC1>[CH2:51]([O:50][C@@H:23]1[C@@H:22]([C:19]([OH:21])([CH3:20])[C:58]([F:61])([F:60])[F:59])[O:30][C@H:29]2[C@H:25]([N:26]=[C:27]([N:31]([CH2:39][CH:40]=[CH2:41])[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[S:28]2)[C@H:24]1[O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 69094256HCID 69094256, compound

Product 1

HCID 69093936HCID 69093936, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of TBAF (1.1, 4.2 mmol) and 4 Å molecular sieves (4 g) in THF (40 mL) was stirred for 30 minutes at 0° C., followed by addition of a mixture of 144 (4.6 g, 8.3 mmol) and CF3TMS (5.9 g, 42 mmol) in THF (40 mL). The mixture was stirred for 3 hours at room temperature, followed by addition of additional TBAF (6 g, 22 mmol). After 1 hour, the reaction was then quenched by addition of water (80 mL). A filtration was performed and the filtrate was extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (2×30 mL), dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography with 6%-12% ethyl acetate in petroleum ether to afford the title compound as a brown syrup (3.5 g, 68%, two isomers, ratio is 1:1 determined by 1H NMR). (ES, m/z): [M+H]+ 623.0; 1H NMR (300 MHz, CDCl3): 7.37-7.23 (m, 10H), 6.13-6.07 (m, 1H), 5.76-5.74 (m, 1H), 5.05-4.92 (m, 2H), 4.74-4.67 (m, 2H), 4.47-4.25 (m, 7H), 3.93-3.88 (m, 1H), 1.50 (s, 9H), 1.28-1.23 (m, 3H).

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. waitAfter 1 hour
  3. customthe reaction was then quenched by addition of water (80 mL)
  4. filtrationA filtration
  5. extractionthe filtrate was extracted with ethyl acetate (3×50 mL)
  6. washThe combined organic layer was washed with brine (2×30 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography with 6%-12% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-fb84c347c52d4ab5a66fdfa445aaa2b9
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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