[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([CH2:11][N:12]3[C:16](=[O:17])[CH2:15][CH2:14][C:13]3=[O:18])[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[CH2:5][N:4]([C:6]2[S:7][CH:8]=[C:9]([CH2:11][N:12]3[C:16](=[O:17])[CH2:15][CH2:14][C:13]3=[O:18])[N:10]=2)[CH2:3]1)(=[O:22])=[O:21]To a solution of 3-hydroxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine (459 mg, 1.72 mmol) (obtained as described in Reference Example 69(2)) in methylene chloride (50 ml) were added methanesulfonyl chloride (0.16 ml, 2.06 mmol) and triethylamine (0.29 ml, 2.06 mmol) in an ice bath and the mixture was stirred 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 sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 3-methanesulfonyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine (515 mg, yield 87%) as a pale yellow solid.
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