Dicyclohexylcarbodiimide → D-Lysine

HRID 879928

Reaction equation

HRID 879928 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16](C(OC(C)(C)C)=O)[C@H:17]([C:23]([O:25]C(C)(C)C)=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]>C(Cl)Cl>[NH2:16][C@@H:17]([C:23]([OH:25])=[O:24])[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 10470194(S)-tert-Butyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate

Product 1

HCID 57449D-Lysine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

One half (0.5) mmol of BOC3(DTPA) was dissolved in 10 ml DCM. 0.6 mmol of DCC was dissolved in 5 ml DCM and added to the BOC3(DTPA) mixture. The reaction was carried out for 1 hour at room temperature. The white crystals that appeared in the mixture were filtered out. 0.5 mmol of solid BOC-Lys-OtBu was added to the reaction. The reaction was carried out for 20 hours at room temperature. The mixture was filtered and the DCM was evaporated. The product was washed several times with ethanol and air-dried. Cleavage of the protecting groups (BOC, OtBu) was carried out in 1 ml TFA (trifluoroacetic acid)+5% water for 3 hours. The acid was evaporated in a vacuum over a KOH pellet. The final product D-Lys(DTPA) was washed several times with diethyl ether and dried. D-Lys(DTPA) was dissolved in water and lyophilized.

Workup

  1. filtrationwere filtered out
  2. waitThe reaction was carried out for 20 hours at room temperature
  3. filtrationThe mixture was filtered
  4. customthe DCM was evaporated
  5. washThe product was washed several times with ethanol
  6. customair-dried
  7. waitCleavage of the protecting groups (BOC, OtBu) was carried out in 1 ml TFA (trifluoroacetic acid)+5% water for 3 hours
  8. customThe acid was evaporated in a vacuum over a KOH pellet
  9. washThe final product D-Lys(DTPA) was washed several times with diethyl ether
  10. customdried
  11. dissolutionD-Lys(DTPA) was dissolved in water

Sources & evidence

ORD record
ord-b976a72da8f34afebb95baffbcbbfb1f
Source dataset
uspto-grants-2015_03
Patent number
US08993278B2

Linked notes

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