Diisopropylcarbodiimide → N-alpha-Benzyloxycarbonyl-L-lysine

HRID 1639475Notes

Reaction equation

HRID 1639475 reaction equation
[C:1]([N:11](C(OCC1C=CC=CC=1)=O)[C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CC(C)N=C=NC(C)C.CC[C@@]1(O)C(=O)OCC2C(N3C(=CC1=2)C1N=C2C(C=CC=C2)=CC=1C3)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:11]([C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 24360CamptothecinHCID 18595285Dicarbobenzoxy-l-lysine

Product 1

HCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N,N-Bis CBZ-Lysine (311 mg, 0.75 mmol) was dissolved in 56 mL of anhydrous methylene chloride at room temperature. To this solution were added DIPC (0.12 mL, 0.75 mmol), DMAP (0.61 mg, 0.5 mmol) and camptothecin (0.087 g, 0.25 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and left for 16 h. The solution was washed with 0.1 N HCl, dried and evaporated under reduced pressure to yield a light yellow solid, which was recrystallized from methanol to give camptothecin-20-ester of N,N-Bis CBZ-Lys 13. Purification of 13 was satisfactory based on TLC and HPLC analysis.

Workup

  1. washThe solution was washed with 0.1 N HCl
  2. customdried
  3. customevaporated under reduced pressure
  4. customto yield a light yellow solid, which
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-d83be793295d48568ed796707dbff9c2
Source dataset
uspto-grants-2012_02
Patent number
US08110179B2

Reaction notes

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