Sulfuric Acid → rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

HRID 604809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604809
[CH2:1]([O:3][C:4]([C@@:6]1([NH:11]C(OC(C)(C)C)=O)[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].S(=O)(=O)(O)O>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C@@:6]1([NH2:11])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 10658673Ethyl (1R,2S)-1-[[(1,1-dimethylethoxy)carbonyl]amino]-2-ethenylcyclopropanecarboxylate

Produkt 1

HCID 10820795rac-ethyl (1R,2S)-1-amino-2-ethenylcyclopropane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
8 °C

Versuchsvorschrift

A suspension of 5.11 g (20.0 mmol) of (1R,2S)-1-tert-butoxycarbonylamino-2-vinyl-cyclopropanecarboxylic acid ethyl ester (commercially available from Synthetech Oregon, USA) in 1.94 mL of ethyl acetate was cooled to 8° C. using an ice bath. Then a solution of 2.17 g (21.0 mmol) of sulfuric acid in 4.0 mL of ethyl acetate was added in 5 min. The ice bath was removed and the reaction mixture was stirred for 30 min at room temperature and 1 h at 50° C. The reaction mixture was then cooled to room temperature and used in the next step without further purification.

Aufarbeitung

  1. customThe ice bath was removed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customused in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-5b44c30be31f4a6fb2d233d6ed607855
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910728B2

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