Methanol → HCID 21993439, Verbindung

HRID 1977578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977578
[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:13]([OH:15])=[O:14])[CH2:8][CH:9]1[CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2].S(Cl)(Cl)=O.[CH3:20]O>>[CH2:1]([O:3][C:4]([NH:6][CH:7]([C:13]([O:15][CH3:20])=[O:14])[CH2:8][CH:9]1[CH2:10][CH2:11][CH2:12]1)=[O:5])[CH3:2]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 21993433HCID 21993433, Verbindung

Produkt 1

HCID 21993439HCID 21993439, Verbindung

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

11 g (51 mmol) of ethoxycarbonyl-3-cyclobutyl-DL-alanine (Example 1, Step A) is dissolved in 100 ml of methanol, cooled to −15° C. and 10 ml (137 mmol) of thionyl chloride is added at constant stirring. Stirring is continued without further cooling. When the reaction mixture reaches room temperature, stirring is continued for further 2 hours. The solution is then evaporated at a pressure of 2.0-2.5 kPa. The residual oil is dissolved in 40 ml of ethyl acetate, washed with 10 ml of 1N HCl, 2×10 ml of 5% NaHCO3 and 2×10 ml of water, dried over anhydrous sodium sulphate and evaporated to dryness at a pressure of 2.0-2.5 kPa. The residue is considered to be pure [yield: 10.8 g (92%), Rf(1)=0.85; Rf(6)=0.65] and is used without further treatment in the next step.

Aufarbeitung

  1. temperaturewithout further cooling
  2. customreaches room temperature
  3. stirringstirring
  4. customThe solution is then evaporated at a pressure of 2.0-2.5 kPa
  5. dissolutionThe residual oil is dissolved in 40 ml of ethyl acetate
  6. washwashed with 10 ml of 1N HCl, 2×10 ml of 5% NaHCO3 and 2×10 ml of water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated to dryness at a pressure of 2.0-2.5 kPa

Quellen und Nachweise

ORD-Eintrag
ord-527e980abb4241f39794b65771c71277
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235707B1

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