2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid → N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

Beteiligte Stoffe

Reaktionsschritte

A suspension of PS-bound N-cyclohexylcarbodiimide (HL 200–400 mesh cross linked with 2% DVB) from Novabiochem (436 mg, 0.841 mmol, 1.93 mmol/g loading) in methylene chloride (6 mL) was treated with 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyric acid (154 mg, 0.480 mmol) in methylene chloride (3 mL) and stirred at room temperature for 10 minutes. A solution of (S)-2-Amino-1-(5-phenyl-1,2,4-oxadiazol-3-yl)-butan-1-ol (96 mg, 0.412 mmol) in methylene chloride (3 mL) was added and the reaction mixture was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was evaporated under reduced pressure. Crude purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide as an off white solid (41 mg) (mixture of diastereoisomers).

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