Scheme 2.
Synthesis of protected antibiotics (8 and 10) suitable for siderophore conjugation.a
aReagents and conditions: (a) N-Boc-O-PNB-Lorabid® (7), TFA, CH2Cl2, 30 min, 99%. (b) ciprofloxacin (9), Boc2O, NaHCO3, DMF, 2.5h; then, BnBr, 90 °C, 25.5 h, 98%. (c) con. HCl, CH2Cl2, 40 min, 92%.