반응 #1137399

반응 방정식

EA

NaH

N-((3R,3aS)-3-(((t-butyldimethylsilyl)oxy)methyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)-acetamide

Iodomethane

→

solid

수율 87.1%

N-((3R,3aS)-3-(((t-butyldimethylsilyl)oxy)methyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)-N-methylacetamide

수율 87.1%

용매

THF

반응 조건

후처리

1. 1
   온도cooled on ice-salt bath
2. 2
   기타The ice bath was removed
3. 3
   온도cooled on ice-salt bath
4. 4
   기타The ice bath was removed
5. 5
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 3 h
6. 6
   기타the reaction
7. 7
   기타the reaction was quenched
8. 8
   workup.ADDITIONby adding 10 ml of water
9. 9
   추출extracted with EA (10 ml×3)
10. 10
    건조dried over anhydrous sodium sulfate
11. 11
    기타the solvent was evaporated

실험 절차

Compound N-((3R,3aS)-3-(((t-butyldimethylsilyl)oxy)methyl)-1-oxo-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-7-yl)-acetamide (0.685 g, 1.747 mmol) was dissolved in 20 ml of THF and cooled on ice-salt bath. 60% NaH (0.14 g, 3.495 mmol) was added. The ice bath was removed, and the reaction mixture was stirred at room temperature for 30 min, and then cooled on ice-salt bath. Iodomethane (0.496 g, 3.495 mmol) was added slowly in dropwise. The ice bath was removed, and the reaction mixture was stirred at room temperature for 3 h. TLC (PE/EA=1/1) was employed to monitor the reaction. After the reaction completed, the reaction was quenched by adding 10 ml of water and then extracted with EA (10 ml×3). The organic phase was combined, dried over anhydrous sodium sulfate, and the solvent was evaporated. Column chromatography (PE/EA=3/1) afforded white solid 0.618 g, yield: 87.11%.

출처