[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[O:7][CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[O:12])[N:10]=2)[CH2:3]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH3:19][S:20]([O:1][CH:2]1[CH2:3][N:4]([C:6]2[O:7][CH:8]=[C:9]([C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[O:12])[N:10]=2)[CH2:5]1)(=[O:22])=[O:21]To a solution of 3-hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (370 mg, 1.48 mmol) (obtained as described in Reference Example 72(2)) in methylene chloride (19 ml) were added methanesulfonyl chloride (344 μl, 4.44 mmol) and triethylamine (622 μl, 4.44 mmol) in an ice bath and the mixture was stirred for 10 minutes and then at room temperature for 1 hour. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium chloride, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (93:7) as the eluant to afford 3-methanesulfonyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (404 mg, yield 100%) as pale yellow crystals.
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