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Synthesis of a modified carbapenem 245. Reagents and conditions: a) AcOEt, LiHMDS, THF, −78 °C, 1.5 h; b) NaBH4, NH4Cl, EtOH/H2O, rt, 1 h; c) H2, Pd(OH)2, EtOH, rt, 4.1 bar, 12 h; d) AcSH, Ph3P, DEAD, THF/DMF, rt, 2 h; e) NaOH, MeOH, 0 °C, 3 min; f) 4-nitrobenzyl (1R,5S,6S)-2-diphenylphosphoryloxy-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate, DIPEA, MeCN, 0–5 °C, 2 h; g) H2, Pd/C, THF/EtOH/Mops buffer, rt, 15 h.
