Acetic Acid → HCID 19856169, compound
Reaction equation
[O-]S([C:5](F)(F)F)(=O)=O.[Na].[SH:10][C:11]1[C:12]([C:21]([O:23][CH3:24])=[O:22])=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18]C=CC=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:24]([O:23][C:21](=[O:22])[C:12]1[CH:13]=[CH:14][C:19]([CH3:18])=[CH:20][C:11]=1[SH:10])[CH3:5]Participants
Conditions
- Temperature
- 90 °C
Procedure
To a solution of the triflate from step A (500 mg, 1.60 mmol) and tetrakistriphenylphosphine palladium(0) (0.05 equiv, 92 mg, 0.08 mmol) in dry benzene (2 mL) under nitrogen at room temperature, a solution of sodium triisopropilsilanethiolate in dry tetrahydrofuran [1.3 equiv, prepared from triisopropilsilanethi61 (396 mg, 2.08 mmol) and sodium hydride (95%, 52 mg, 2.08 mmol) in tetrahydrofuran (2 mL) as in Example 22, Step B] was added and the reaction mixture was warmed to reflux (bath temp 90° C.) for 3.5 h. The reaction mixture was cooled down to 0° C. and tetrabutylammonium fluoride (1 M solution in tetrahydrofuran, 1.5 equiv, 3.1 mL, 3.1 mmol) and glacial acetic acid (3.5 equiv, 437 mg, 0.405 mL, 7.28 mmol) were added and the reaction mixture stirred at 0° C. for 20 min. Work-up as in Example 22, Step B gave, after flash chromatography (silica gel, hexane-ethyl acetate 25:1), the desired thiol as an oil (220 mg, 70%). The product was kept under nitrogen at −18° C.
Workup
- temperaturethe reaction mixture was warmed
- temperatureThe reaction mixture was cooled down to 0° C.
- customgave
- customwas kept under nitrogen at −18° C.
Sources & evidence
- ORD record
- ord-87c1225e93f44acd9dbf1daec6f1a250
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07205313B2
Reaction notes
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