Hydrochloric Acid → HCID 18611977, compound

Participants

Reaction Steps

Reaction of the iodide 21 with diethylphthalimidomalonate yields ethyl 2,6-diphthalimido-2-ethoxycarbonyl-5-fluoro-7-octenoate, 22. Removal of the amino-protecting groups leads to ethyl 2,6-diamino-2-ethoxycarbonyl-5-fluoro-7-octenoate, 23. Acid hydrolysis of 23 yields 2,6-diamino-2-carboxy-5-fluoro-7-octenoic acid 24, which is decarboxylated by heating with acetic acid in the presence of hydrochloric acid to yield δ-fluoro-ε-vinyllysine, 25. Protection of the amino groups wih di-tert-butyl dicarbonate and triethylamine results in the preparation of Nα,Nε -di-tert-butoxycarbonylamino-δ-fluoro-ε-vinyllysine, 26, which upon oxidation with potassium permanganate yields Nα,Nε -di-tert-butoxycarbonylamino-δ-fluoro-ε-carboxylysine, 27. Removal of the protecting group with HCl results in the desired δ-fluoro-ε-carboxylysine, 2.

Provenance & Evidence