Sodium hydride → HCID 11950680, compound

To a solution of triisopropylsilane thiol (0.91 mmol) in anhydrous THF (2 ml) was added sodium hydride (0.68 mmol, 60% in mineral oil) and the reaction mixture was stirred at room temperature for 15 min. Afterwards, compound 109 (0.45 mmol, dissolved in 2 ml THF) was added to the reaction and the mixture was stirred at room temperature for 1 h. Then it was concentrated in vacuo, diluted with ethyl acetate and washed with sodium bicarbonate. The layers were separated and the organic layer was dried over magnesium sulfate and concentrated in vacuo. Column chromatography purification (12 g pre-packed silica column, hexane/ethyl acetate) afforded the protected thiol. The thiol (0.126 mmol) was then diluted with anhydrous methanol (2 ml) and ammonium fluoride (0.15 mmol, 0.5 M in methanol) and acetic acid (0.454 mmol) were added to the reaction and the mixture was stirred at room temperature for 2 h. Afterwards, it was concentrated in vacuo and the residual acetic acid was azeotroped with toluene. The solid was diluted with dichloromethane and was filtered through a syringe filter. The solution was concentrated in vacuo to give compound 110 as a clear oil (23% yield for both steps). LS/MS M+H 282.3, calc. 282.1.

1. stirringthe mixture was stirred at room temperature for 1 h
2. concentrationThen it was concentrated in vacuo
3. additiondiluted with ethyl acetate
4. washwashed with sodium bicarbonate
5. customThe layers were separated
6. dry with materialthe organic layer was dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customColumn chromatography purification (12 g pre-packed silica column, hexane/ethyl acetate)

ORD record

ord-1a533b3d88814afb96514de5a313d730

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501404B2