Camptosar → Irinotecan

HRID 1614850

Reaction equation

HRID 1614850 reaction equation
[CH3:1][CH2:2][C:3]1[C:12]2[CH2:13][N:14]3[C:19](=[O:20])[C:18]4[CH2:21][O:22][C:23]([C@:25]([OH:28])([CH2:26][CH3:27])[C:17]=4[CH:16]=[C:15]3[C:11]=2[N:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:34][CH2:33]1)=[O:31])[CH:7]=[CH:8]2)=[O:24].O.O.O.Cl.[Na].N[C@H](C(O)=O)CS(=O)(O)=O>CO>[CH3:1][CH2:2][C:3]1[C:12]2[CH2:13][N:14]3[C:19](=[O:20])[C:18]4[CH2:21][O:22][C:23]([C@:25]([OH:28])([CH2:26][CH3:27])[C:17]=4[CH:16]=[C:15]3[C:11]=2[N:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([O:29][C:30]([N:32]1[CH2:33][CH2:34][CH:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[CH2:36][CH2:37]1)=[O:31])[CH:7]=[CH:8]2)=[O:24]

Participants

5

Reactant 3

HCID 60837CamptosarHCID 72886L-Cysteic acidHCID 5360545Sodium

Product 1

HCID 60838Irinotecan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customevaporated in vacuo
  2. addition100 ml of water was added to the residue
  3. customobtained
  4. customafter evaporation
  5. customtransparent (approx. 30 min)
  6. filtrationThe obtained solution was filtered through 0.2 mm
  7. filtrationfilter
  8. customfreeze dried
  9. filtrationThe filtration

Sources & evidence

ORD record
ord-170cc3a8259f48feaeec895636c2ce05
Source dataset
uspto-grants-2014_07
Patent number
US08765173B2

Linked notes

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