[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:18](N(CC)CC)C.S(Cl)(Cl)=O.CO>C1COCC1.CCOC(C)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1
To a stirred solution of 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylic acid (0.75 g, 2.06 mmol) in THF (15 mL) is added triethylamine (0.43 mL, 3.09 mmol) followed by thionyl chloride (0.18 mL, 2.47 mmol). After stirring for 1 h, MeOH (10 mL) is added. Stirring is continued for another 1 h. The reaction mixture is concentrated under reduced pressure to give a residue which is taken up in EtOAc and washed with saturated aqueous NaHCO3. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure to give 0.60 g (77%) of methyl 1-[(4-iodophenyl)sulfonyl]azetidine-3-carboxylate. m/z=382 [M++H].
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