Reacción #48794

Ecuación de reacción

sodium thiosulfate pentahydrate

Trimethylsilyl iodide

3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

Methanol

→

title compound

Rendimiento 65.6%

3-Hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide

Rendimiento 65.6%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench
2. 2
   Otrothe reaction
3. 3
   workup.STIRRINGstirred for 10 mins
4. 4
   workup.ADDITIONwas added to the mixture
5. 5
   Otrothe organic solvents removed in vacuo
6. 6
   workup.ADDITIONadded
7. 7
   OtroA yellow solid (1.4 g) was separated by filtration
8. 8
   Secadothe combined organic layers dried (MgSO4)
9. 9
   Filtraciónfiltered
10. 10
    Otrothe solvents removed in vacuo
11. 11
    Otroobtained above and
12. 12
    Otropurified by column chromatography
13. 13
    Lavadoeluting with 5% to 10% methanol in DCM

Procedimiento

Trimethylsilyl iodide (6.06 mL, 42.75 mmol) was added to a solution of 3-hydroxy-5-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-N-(5-methylpyrazin-2-yl)benzamide (2.71 g, 8.55 mmol) in dry acetonitrile (150 mL) and stirred for 24 h. Methanol (30 mL) was added to quench the reaction and stirred for 10 mins. 10% w/v Aqueous sodium thiosulfate pentahydrate (20 mL) was added to the mixture and the organic solvents removed in vacuo. The residue was brought to pH5 with 1M hydrochloric acid and ethyl acetate (80 mL) added. A yellow solid (1.4 g) was separated by filtration. The aqueous filtrate was reextracted into ethyl acetate (2×80 mL) and the combined organic layers dried (MgSO4), filtered and the solvents removed in vacuo. This residue was combined with the yellow solid obtained above and purified by column chromatography, eluting with 5% to 10% methanol in DCM, to give the title compound (1.70 g)

Fuente