Sodium Hydroxide → 2-[(4-{2-[(5-Carboxy-3-chloropyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

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Reaction Steps

2-[(4-{2-[[3-Chloro-5-(methoxycarbonyl)pyridin-2-yl](heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (2.50 g) obtained in Example 281-1 was dissolved in ethanol (25 mL), 1N aqueous sodium hydroxide solution (5 mL) was added, and the mixture was left standing for 12 hr. The reaction mixture was concentrated, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; chloroform:methanol=50:1) to give 2-[(4-{2-[(5-carboxy-3-chloropyridin-2-yl)(heptyl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (2.5 g) as a colorless oil. Without purification, the present compound was dissolved in dichloromethane (20 mL), WSCD (0.72 g) and ammonia/methanol solution (7M, 1 mL) was added, and the mixture was stirred at room temperature for 12 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:2) to give the title compound (0.86 g) as a colorless oil.

Provenance & Evidence