3-Octene → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

関与物質

反応条件

反応手順

A solution of the Z form of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene and -oct-3-ene (0.22 g) in methylene chloride (10 cc) is cooled to 0° C. A solution of 85% pure m-chloroperbenzoic acid (0.07 g) in methylene chloride (5 cc) is added dropwise in the course of 20 minutes. The solution is then stirred for 5 minutes at 0° C., washed with a saturated solution of sodium bicarbonate (20 cc), dried over sodium sulphate and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. The residue is chromatographed on a column of Merck silica gel (0.06-0.2) (4 g) (diameter of the column: 1 cm; height: 10 cm). Elution is carried out with a 60/40 (by volume) ethyl acetate/cyclohexane mixture (100 cc) and and 3 cc fractions are collected. Fractions 11 to 22 are concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields the Z form of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (0.12 g) in the form of a hard white foam.

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