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Citric Acid → Ethyl 3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-4-nitrobutanoate

HRID 1279647
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1279647
[CH2:1]([O:8][CH:9]1[CH2:12][C:11](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C.[N+:69]([CH3:72])([O-:71])=[O:70]>>[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH:21]([CH2:72][N+:69]([O-:71])=[O:70])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 311Citric AcidHCID 6375NitromethaneHCID 8857Ethyl AcetateHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 86758504Ethyl (E)-3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]acrylate

Produkt 1

HCID 18427804
Ethyl 3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-4-nitrobutanoate
Ausbeute 97,2 %

Versuchsvorschrift

A 31.07 g (82.75 mmol) portion of ethyl (E)-3-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]acrylate was dissolved in 300 ml of nitromethane to which, while cooling in an ice bath with stirring, was subsequently added dropwise 13.37 ml (82.75 mmol) of diazabicycloundecene. After 10 minutes of stirring, the ice bath was detached and the reaction mixture was stirred at room temperature for 1 hour. While cooling in an ice bath with stirring, the reaction solution was acidified by gradually adding 10% citric acid aqueous solution and then mixed with ethyl acetate to effect separation of layers. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and then with saturated brine. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under a reduced pressure to give 35.12 g (97.2%) of the title compound. This compound was used in the following reaction without purification.

Aufarbeitung

  1. temperaturewhile cooling in an ice bath
  2. stirringAfter 10 minutes of stirring
  3. stirringthe reaction mixture was stirred at room temperature for 1 hour
  4. temperatureWhile cooling in an ice bath
  5. stirringwith stirring
  6. customseparation of layers
  7. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was evaporated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-04005fcfd4534669b6aa2ffd9d245df5
Quelldatensatz
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06448266B1

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