2-[N-tert-butoxycarbonyl-N-{3-methoxycarbonyl-1-[3-(2-propenyloxycarbonylamino)phenyl]propyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine → 2-[N-tert-butoxycarbonyl-N-{4-hydroxy-1-[3-(2-propenyloxycarbonylamino)phenyl]butyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine

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2-[N-tert-butoxycarbonyl-N-{3-methoxycarbonyl-1-[3-(2-propenyloxycarbonylamino)phenyl]propyl}amino]-6-(5-ethyl-1,3,4-thiadiazol-2-ylthiomethyl)-4-morpholinopyridine (100 mg) obtained in Example 138-(2) was dissolved in tetrahydrofuran (3 ml), and a 2 M lithium borohydride-tetrahydrofuran solution (0.1 ml) was added thereto, followed by stirring at room temperature for 15 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to obtain the above identified compound (66 mg).

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