[C:1]1([C@H:7]([N:9]2[C:13](=[O:14])[CH2:12][C@@H:11]([C:15]([OH:17])=O)[CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](Cl)(=[O:22])C(Cl)=O.[CH2:24]([N:26](CC)CC)C>CN(C)C=O.ClCCl>[CH3:24][N:26]([O:22][CH3:18])[C:15]([C@@H:11]1[CH2:12][C:13](=[O:14])[N:9]([C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[CH2:10]1)=[O:17]To a dichloromethane solution (200 ml) of 1-[1-(R)-phenylethyl]-5-oxopyrrolidine-3-(R)-carboxylic acid (11.66 g, 0.05 mol) were added oxalyl chloride (6.54 ml, 0.075 mol) and dimethylformamide (3 drops) under ice cooling, followed by stirring at room temperature overnight. After removal of the solvent under reduced pressure, toluene (100 ml) was added thereto and the solvent was again removed under reduced pressure. To the residue were added dichloromethane (200 ml) and N,O-methylhydroxylamine hydrochloride (5.47 g, 0.055 mol), and then a dichloromethane solution (50 ml) of triethylamine (17.4 ml, 0.125 mol) was added thereto under ice cooling and stirring over a period of 15 minutes. After stirring under ice cooling for 30 minutes, the mixture was stirred at room temperature for 3 hours. The reaction solution was washed with 10% citric acid aqueous solution (100 ml), water (100 ml) and saturated sodium hydrogen carbonate aqueous solution (100 ml), successively, and then dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. Elution with chloroform/methanol of 50/1 to 20/1 afforded the title compound (11.32 g, 82%) as a brown oil.
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