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The key synthetic steps of the synthesis of cefaclor® by Eli Lilly Company. PG = protecting group. Reagents and conditions: (a) NCS, toluene, reflux; (b) SnCl4, CH2Cl2, rt; (c) O3, CH2Cl2, −70 °C; (d) (PhO)3PCl2, CH2Cl2, −15 °C then iBuOH; (e) 2-amino-2-phenylacetylchloride; deprotection.
