Water → (3-tert-Butoxycarbonylamino-cyclobutylidene)-acetic acid methyl ester

HRID 1050995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050995
[C:1]([O:5][C:6](=[O:13])[NH:7][CH:8]1[CH2:11][C:10](=O)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1(P(=[CH:33][C:34]([O:36][CH3:37])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:37][O:36][C:34](=[O:35])[CH:33]=[C:10]1[CH2:11][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13])[CH2:9]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 23374584tert-Butyl 3-oxocyclobutylcarbamate

Produkt 1

HCID 23374583(3-tert-Butoxycarbonylamino-cyclobutylidene)-acetic acid methyl esterAusbeute 1.450,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (3-oxo-cyclobutyl)-carbamic acid tert-butyl ester (5.6 g, 30 2 mmol) in anhydrous toluene (100 mL) was added methyl (triphenylphosphoranylidene)acetate (10.7 g, 45.4 mmol) and heated to reflux overnight under N2. After cooling to room temperature, the mixture was poured into water and extracted with EA. The organic phase was dried over Na2SO4, concentrated under reduced pressure to give a residue, which was purified by column chromatography on silica gel (eluted with PE:EA=20:1) to give the title compound (7 g, yield 96%) as a white solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight under N2
  3. extractionextracted with EA
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue, which
  7. customwas purified by column chromatography on silica gel (eluted with PE:EA=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-12270812d1804ee3aadb417f20cc2b9a
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388148B2

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