Reaktion #2018

Reaktionsgleichung

ethyl acetate

allyl alcohol

N-(t-Butoxycarbonyl)-O-benzyl-D-serine

EDC

→

N-(t-Butoxycarbonyl)-O-Benzyl-D-Serine Allyl Ester

Lösungsmittel

—

hexanes

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting homogeneous solution quenched with water
2. 2
   Extraktionextracted with methylene chloride
3. 3
   WaschenThe methylene chloride layer was washed with 5% aqueous citric acid
4. 4
   TrocknenThe methylene chloride layer was dried over anhydrous magnesium sulfate powder
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under reduced pressure
7. 7
   Sonstigeto give an oil
8. 8
   Sonstigeafforded the product (408 mg; 60%) as a pale yellow gum

Vorschrift

N-(t-Butoxycarbonyl)-O-benzyl-D-serine (600 mg; 2.03 mmol) was dissolved in dry methylene chloride (5 ml), allyl alcohol (152 μl; 2.23 mmol) and DMAP (25 mg; 0.20 mmol) added and finally EDC (428.5 mg; 2.24 mmol) added to the acid. The reaction mixture was stirred at room temperature for 2.5 h and the resulting homogeneous solution quenched with water and extracted with methylene chloride. The methylene chloride layer was washed with 5% aqueous citric acid then 10% aqueous sodium carbonate solution. The methylene chloride layer was dried over anhydrous magnesium sulfate powder, filtered and evaporated under reduced pressure to give an oil. Chromatography of the oil using ethyl acetate and hexanes 1:2 v/v afforded the product (408 mg; 60%) as a pale yellow gum. FAB-MS:- Calculated for C36H33N5 335.1; found 336.1 (M+1).

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