반응 #48794

반응 방정식

sodium thiosulfate pentahydrate

Trimethylsilyl iodide

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

Methanol

→

title compound

수율 65.6%

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

수율 65.6%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   workup.STIRRINGstirred for 10 mins
4. 4
   workup.ADDITIONwas added to the mixture
5. 5
   기타the organic solvents removed in vacuo
6. 6
   workup.ADDITIONadded
7. 7
   기타A yellow solid (1.4 g) was separated by filtration
8. 8
   건조the combined organic layers dried (MgSO4)
9. 9
   여과filtered
10. 10
    기타the solvents removed in vacuo
11. 11
    기타obtained above and
12. 12
    기타purified by column chromatography
13. 13
    세척eluting with 5% to 10% methanol in DCM

실험 절차

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)

출처