Hydrochloric Acid → HCID 18611977, compound

HRID 568964Notes

Reaction equation

HRID 568964 reaction equation
[NH2:1][C:2](C(O)=O)([CH2:6][CH2:7][CH:8]([F:13])[CH:9]([NH2:12])[CH:10]=[CH2:11])[C:3]([OH:5])=[O:4].Cl>C(O)(=O)C>[F:13][CH:8]([CH:9]([CH:10]=[CH2:11])[NH2:12])[CH2:7][CH2:6][C@@H:2]([C:3]([OH:5])=[O:4])[NH2:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20149481HCID 20149481, compound

Product 1

HCID 18611977HCID 18611977, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  1. customRemoval of the amino-
  2. customAcid hydrolysis of 23

Sources & evidence

ORD record
ord-71a1ace8f42f4448a2496a713741fd86
Source dataset
uspto-grants-1988_03
Patent number
US04730006

Reaction notes

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