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0 °C

In a mixed solvent of THF (250 ml) and water (125 ml), (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester (9.80 g) was dissolved, and the resulting mixture was cooled to 0° C. Barium hydroxide octahydrate (3.14 g) was added thereto and the resulting mixture was stirred at 0° C. for 8 hours. The reaction solution was concentrated to remove THF, and water (150 ml) was added thereto, followed by washing the resulting mixture with ether. Aqueous layer was acidified by adding 1N hydrochloric acid in small portions thereto and extracted 3 times with ethyl acetate. Organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: chloroform/methanol=10/1). The obtained crude product was further purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=1/1→ethyl acetate) to obtain (S,E)-2-(2,6-dichlorobenzamido)-5-[4-(4-methoxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid (6.15 g).

1. concentrationThe reaction solution was concentrated
2. customto remove THF, and water (150 ml)
3. additionwas added
4. washby washing the resulting mixture with ether
5. additionby adding 1N hydrochloric acid in small portions
6. extractionextracted 3 times with ethyl acetate
7. washOrganic layers were washed with saturated brine
8. dry with materialdried over anhydrous sodium sulfate
9. customAfter removing anhydrous sodium sulfate
10. filtrationby filtration
11. concentrationthe filtrate was concentrated
12. customThe residue was purified by column chromatography (silica gel, eluent: chloroform/methanol=10/1)
13. customThe obtained crude product
14. customwas further purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate=1/1→ethyl acetate)