Ethanol → ethyl (2S)-2-amino-2-cyclopropylacetate

HRID 2366352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366352
S(=O)(=O)(O)O.[NH2:6][C@@H:7]([CH:11]1[CH2:13][CH2:12]1)[C:8]([OH:10])=[O:9].[CH2:14](O)[CH3:15]>>[NH2:6][C@@H:7]([CH:11]1[CH2:13][CH2:12]1)[C:8]([O:10][CH2:14][CH3:15])=[O:9]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1501944(2S)-2-amino-2-cyclopropylacetic acid

Produkt 1

HCID 51611535ethyl (2S)-2-amino-2-cyclopropylacetate

Versuchsvorschrift

Sulfuric acid (conc., 1.704 g, 0.926 mL, 17.37 mmol) was added to a solution of (S)-2-amino-2-cyclopropylacetic acid (1 g, 8.69 mmol) in ethanol (12 mL) and heated to reflux for 5 h, then cooled to rt. The reaction mixture was concentrated under vacuum to remove solvent and water (10 mL) was added. The pH of the mixture was adjusted to 10 using 2M aq. sodium hydroxide and was then extracted with DCM (3×15 mL). The organic phase was dried with sodium sulfate and concentrated under vacuum to provide (S)-ethyl 2-amino-2-cyclopropylacetate (862 mg) which was used as is.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 5 h
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customto remove solvent and water (10 mL)
  5. additionwas added
  6. extractionwas then extracted with DCM (3×15 mL)
  7. dry with materialThe organic phase was dried with sodium sulfate
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8c9f3814bf5b46f5b4c9db9d1bab6b5c
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697739B2

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