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0 °C

To a solution of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine (0.5 g) in dimethylformamide (5 ml) was added K2CO3 (75 mg) under stirring at 0° C., stirred for 15 minutes, and pivalic acid iodomethyl ester (0.61 g) in dimethylformamide (3 ml) was added to the mixture. After stirring at room temperature for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, dried over MgSO41 and evaporated in vacuo, subsequently. The residue was purified by column chromatography on silica gel eluting with CHCl3:MeOH=(98:2) to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine pivaloyloxymethyl ester as a colorless oil (0.37 g, 59.3%).

1. stirringstirred for 15 minutes
2. stirringAfter stirring at room temperature for 1 hour
3. extractionextracted with ethyl acetate
4. washThe extract was washed with water and brine
5. customdried over MgSO41
6. customevaporated in vacuo
7. customThe residue was purified by column chromatography on silica gel eluting with CHCl3