Reaktion #1253201

Reaktionsgleichung

thionyl chloride

thionyl chloride

L-arginine

octanol

thionyl chloride

→

arginine octyl ester

Ausbeute 85.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe temperature was maintained
2. 2
   TemperaturThe mixture was cooled to 60° C
3. 3
   workup.STIRRINGthe mixture was stirred at 60° C. for an additional 2 hours, at which time the reaction
4. 4
   Sonstigeto evaporate
5. 5
   TemperaturThen, the solution was cooled to room temperature
6. 6
   workup.ADDITION250 ml diethyl ether was added
7. 7
   WaschenWashing of the resultant soft white precipitate with saturated sodium bicarbonate solution
8. 8
   Sonstigegave a white solid
9. 9
   FiltrationFiltration of this suspension
10. 10
    Waschenwashing of the filtrate with saturated sodium bicarbonate solution (3× with 20 ml), water (3× with 20 ml), acetone (3× with 20 ml) and diethyl ether (3× with 20 ml)

Vorschrift

One millimole thionyl chloride was added to a stirred suspension of one millimole L-arginine free base in 50 mL of octanol under nitrogen. The mixture was heated to 90° C, and the temperature was maintained with stirring for 2 hours. The mixture was cooled to 60° C, one more equivalent of thionyl chloride was added, and the mixture was stirred at 60° C. for an additional 2 hours, at which time the reaction was seen to be complete by TLC (performed as described in Example 33). Excess thionyl chloride was allowed to evaporate. Then, the solution was cooled to room temperature, and 250 ml diethyl ether was added. Washing of the resultant soft white precipitate with saturated sodium bicarbonate solution gave a white solid. Filtration of this suspension and washing of the filtrate with saturated sodium bicarbonate solution (3× with 20 ml), water (3× with 20 ml), acetone (3× with 20 ml) and diethyl ether (3× with 20 ml) gave arginine octyl ester. The yield was 85%. FAB mass spectrometry gave the expected parameters for arginine octyl ester.

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