C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]([OH:16])=O)=[O:10].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.O>ClCCl.CN(C)C=O>[C:22]1([CH2:21][O:20][C:19]2[CH:18]=[CH:17][C:13]([C:14]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:16])=[CH:12][C:11]=2[C:9]([O:8][CH3:7])=[O:10])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
Oxalyl chloride (0.61 ml, 6.99 mmol) was added dropwise to a stirred solution of 3-[(methyloxy)carbonyl]-4-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 49; 400 mg, 1.40 mmol) in dichloromethane (10 ml) and dimethylformamide (3 drops) at room temperature. The mixture was stirred at room temperature for 1 h. The solvent was removed, and the residue was dissolved in dichloromethane (5 ml). This mixture was added to a solution of pyrrolidine (497 mg, 6.99 mmol) in dichloromethane (5 ml) and the mixture was stirred at room temperature for 2 h. Water (60 ml) was added, and the mixture was extracted with dichloromethane (3×60 ml). The organic phase was washed with saturated brine (50 ml), dried over sodium sulfate, and evaporated in vacuo to give the crude product. The crude product was loaded onto a silica gel column (200 g), and was eluted with dichloromethane/methanol=50:1 to yield the title compound as a colourless oil. 400 mg.
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