[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][OH:14])[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17].[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][S:21]([CH3:20])(=[O:23])=[O:22])[CH:7]=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17]
To a solution of 2-acetylamino-5-(3-hydroxypropoxy)benzoic acid methyl ester (689 mg, 2.6 mmol) in dichloromethane (25 mL) cooled to 0° C. were added methanesulfonyl chloride (1 mL, 12.9 mmol) and triethylamine (3.6 mL, 25.8 mmol). The mixture was warmed to room temperature and stirred for 2.5 h. The mixture was diluted with ethyl acetate (100 mL) and washed with 1 N HCl (aq.) (1×50 mL), sat. NaHCO3 (aq.) (1×50 mL) and brine (1×50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Crude 2-acetylamino-5-(3-methanesulfonyloxypropoxy)benzoic acid methyl ester thus obtained was used without further purification in the next step.
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