Lithium Hydroxide → 3-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid

HRID 1975052

반응식

HRID 1975052 반응식
[C:1]([O:5][C:6]([N:8]1[C:11]([CH3:13])([CH3:12])[CH2:10][C:9]1=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:15].[Li+]>O1CCCC1.CCOCC.O>[C:1]([O:5][C:6]([NH:8][C:11]([CH3:13])([CH3:12])[CH2:10][C:9]([OH:14])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 10397866Tert-butyl 2,2-dimethyl-4-oxoazetidine-1-carboxylate

생성물 1

HCID 103760463-((tert-Butoxycarbonyl)amino)-3-methylbutanoic acid수율 87%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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%).

후처리

  1. customA 3 L, 3-neck round bottom flask equipped with a magnetic stirrer
  2. additionthermometer, nitrogen bubbler and addition funnel
  3. temperatureThe solution was cooled to 0°-5° C.
  4. customto separate
  5. additionThe aqueous layer was acidified by the addition of 1 L of saturated aqueous sodium bisulfate
  6. extractionextracted with 1×1 L and 2×500 mL of ether
  7. washThe combined organic layer and ether extracts were washed with 500 mL of saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under vacuum to 173 g of a yellow oil
  10. filtrationthen filtered
  11. customdried under high vacuum

출처 및 근거

ORD 기록
ord-a453462afe20409693bf792131cbc2a6
출처 데이터셋
uspto-grants-1994_02
특허 번호
US05284841

연결된 노트

불러오는 중…