Reaction #1702032

ord-170cc3a8259f48feaeec895636c2ce05

Reaction equation

CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC.Cl.O.O.O
irinotecan hydrochloride trihydrate
[Na]
sodium
N[C@@H](CS(=O)(=O)O)C(=O)O
cysteic acid
CCc1c2c(nc3ccc(OC(=O)N4CCC(N5CCCCC5)CC4)cc13)-c1cc3c(c(=O)n1C2)COC(=O)[C@]3(O)CC
irinotecan

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherevaporated in vacuo
  2. 2
    workup.ADDITION100 ml of water was added to the residue
  3. 3
    Otherobtained
  4. 4
    Otherafter evaporation
  5. 5
    Othertransparent (approx. 30 min)
  6. 6
    FiltrationThe obtained solution was filtered through 0.2 mm
  7. 7
    Filtrationfilter
  8. 8
    Otherfreeze dried
  9. 9
    FiltrationThe filtration

Procedure

Methanol stock-solutions of irinotecan hydrochloride trihydrate (100 ml, 1.15 mg/ml) and sodium salt of methyl ester of N-all-trans-retinoyl cysteic acid (27 ml, 15 mg/ml) were mixed in a 500 ml round-bottom flask and evaporated in vacuo. 100 ml of water was added to the residue obtained after evaporation and the mixture was stirred until it became clear and transparent (approx. 30 min). The concentration of irinotecan in the obtained solution was 1 mg/ml, corresponding to an irinotecan hydrochloride trihydrate concentration of 1.15 mg/ml. The obtained solution was filtered through 0.2 mm filter and freeze dried. The filtration did not result in reduction of irinotecan concentration.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08765173B2uspto-grants-2014_07