반응 #1579926

반응 방정식

N-(t-butoxycarbonyl)-4,4-dimethylazetidin-2-one

lithium hydroxide

→

product

수율 87.0%

3-t-Butoxycarbonylamino-3-methylbutanoic acid

수율 87.0%

용매

ether

water

tetrahydrofuran

반응 조건

후처리

1. 1
   기타A 3 L, 3-neck round bottom flask equipped with a magnetic stirrer
2. 2
   workup.ADDITIONthermometer, nitrogen bubbler and addition funnel
3. 3
   온도The solution was cooled to 0°-5° C.
4. 4
   기타to separate
5. 5
   workup.ADDITIONThe aqueous layer was acidified by the addition of 1 L of saturated aqueous sodium bisulfate
6. 6
   추출extracted with 1×1 L and 2×500 mL of ether
7. 7
   세척The combined organic layer and ether extracts were washed with 500 mL of saturated aqueous sodium chloride
8. 8
   건조dried over magnesium sulfate
9. 9
   농축concentrated under vacuum to 173 g of a yellow oil
10. 10
    여과then filtered
11. 11
    기타dried under high vacuum

실험 절차

A 3 L, 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, nitrogen bubbler and addition funnel was charged with 180.3 g (0.89 mol) of N-(t-butoxycarbonyl)-4,4-dimethylazetidin-2-one dissolved in 1 L of tetrahydrofuran. The solution was cooled to 0°-5° C. and treated dropwise with 890 mL of 1.0M aqueous lithium hydroxide over 30 minutes. The reaction mixture was stirred at 0°-5° C. for 2 hours then diluted with 1 L of ether and 1 L of water. The layers were allowed to separate and the aqueous layer reextracted with an additional 1 L of ether. The aqueous layer was acidified by the addition of 1 L of saturated aqueous sodium bisulfate, then extracted with 1×1 L and 2×500 mL of ether. The combined organic layer and ether extracts were washed with 500 mL of saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under vacuum to 173 g of a yellow oil that solidified upon standing. The material was slurried with warm hexane then filtered and dried under high vacuum to afford 168.5 g (0.775 mol,87%) of product as a white solid. 1H NMR (200 MHz,CDCl3): 1.39 (s,6H), 1.44 (s,9H), 2.72(s,2H). FAB-MS: calculated for C10H19NO4 217; found 218 (M+H,54%).

출처