P(Cl)(Cl)(Cl)(Cl)Cl.COC1C=CC(C[O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[CH:24]([NH:25]C(=O)CC4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[CH:36]=[CH:37][CH3:38])=[O:16])=CC=1.C(O)C(O)C.C1(C)C(O)=CC=CC=1>O.N1C=CC=CC=1.C(Cl)Cl>[NH2:25][CH:24]1[C:23](=[O:35])[N:22]2[C:17]([C:15]([OH:16])=[O:14])=[C:18]([CH:36]=[CH:37][CH3:38])[CH2:19][S:20][C@H:21]12
22.8 g of phosphorus pentachloride, 150 ml of methylenechloride, and 8.88 ml of pyridine were placed in a 20° C. reactor and stirred for 30 minutes. 30 g (62.6 mmol) of the 7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester prepared in Example 2 was dropwise added thereto and stirred for 2 hours. The reaction mixture was cooled to −10° C. and was stirred for 2 hours after addition of 30 ml of 1,2-propanediol and then for 2 hours after addition of 120 ml of cresol. 200 ml of distilled water was dropwise added thereto and stirred for 1 hour. After phase separation, an aqueous layer was sent to a crystallization bath, and an organic layer was extracted with 300 ml of 2N HCl and then the extract was sent to the crystallization bath. 200 ml of a 30% sodium hydroxide solution was dropwise added to the crystallization bath for crystallization and then cooled to 0° C. An obtained solid was filtered and dried in vacuum to give 12 g (50 mmol, yield 80%, Z/E=10.1/1) of the titled compound as a beige solid.
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