C(O[C@H](C)[C@H](NC(C1(CC2C=CC=CC=2)CCCN1)=O)C(OC)=O)(=O)C.C([O-])([O-])=O.[Na+].[Na+].[CH2:33]([O:40][C:41]([N:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[C:48]([OH:50])=O)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O=S(Cl)[Cl:53]>C(Cl)Cl.O>[Cl:53][C:48]([C@@H:44]1[CH2:45][CH2:46][CH2:47][N:43]1[C:41]([O:40][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:42])=[O:50]To a stirred solution of compound 6 (1 g, 2.76 mmol) and Na2CO3 (732 mg, 6.90 mmol) in CH2Cl2:H2O (20 mL, 1:1) was added a solution of acid chloride [To a solution of (S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (825 mg, 3.31 mmol) in CH2Cl2 (20 mL) was added SOCl2 (0.60 mL) drop wise at 0° C. and was refluxed for 2 h. The volatiles were removed under reduced pressure to yield (S)-benzyl 2-(chlorocarbonyl)pyrrolidine-1-carboxylate] in CH2Cl2 and the reaction mixture was stirred at RT for 2 h. The volatiles were evaporated under reduced pressure. The residue was diluted with CH2Cl2 (100 mL), filtered and the filtrate was concentrated under vacuum. The crude residue was purified by column chromatography using 60% EtOAc/Hexane as eluent to afford compound 7 (750 mg, 45%).
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