Hydrochloric Acid → Camptosar

HRID 2115183

Reaction equation

HRID 2115183 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].C([O-])(=[O:46])C.C([OH:50])C.[ClH:51]>C(OCC)(=O)C>[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].[OH2:46].[OH2:50].[OH2:20].[ClH:51]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131727091Irinotecan acetate

Product 1

HCID 60837Camptosar

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suitable vessel were charged amorphous irinotecan acetate (14.5 g) and ethanol (101 mL). The resulting mixture was heated to reflux and remained as a suspension. 2N HCl (10 mL) was added to the reaction mixture to adjust the pH to less than 4. Ethyl Acetate (145 mL) was added to the resulting mixture. The mixture was then cooled to 0˜10° C. and stirred at this temperature for 1 hour, filtrated, and washed with ethyl acetate (100 mL). The solid was then dried in vacuum. Due to a lower than expected water content, the solid was put under atmosphere overnight to give irinotecan hydrochloride trihydrate Form II (13.5 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was then cooled to 0˜10° C.
  4. filtrationfiltrated
  5. washwashed with ethyl acetate (100 mL)
  6. customThe solid was then dried in vacuum
  7. customwas put under atmosphere overnight

Sources & evidence

ORD record
ord-35b4fd6fc08c495081886578c5bef902
Source dataset
uspto-grants-2008_10
Patent number
US07435818B2

Linked notes

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