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

HRID 1492744

Reaktionsgleichung

Reaktionsgleichung von HRID 1492744
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e60633ff986c458dac30a4bbed3ba87f
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05374721

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