Acetone → Irinotecan Hydrochloride

HRID 1724885Notes

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].CC(C)=O.[ClH:48]>C(#N)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].[ClH:48]

Participants

Conditions

Temperature: 22 °C

Procedure

Irinotecan was suspended in acetonitrile or acetone in accordance with the amounts shown in Table 1 and dissolved by adding, 6 mol/L hydrochloric acid. To each mixture solution, 1 mg of c-type crystals separately prepared was added and the solution was stirred at 22° C. for 25 to 46 hours. The formed crystals were obtained by filtration, dried under reduced pressure, and subjected to a moisture absorption process performed by a saturated aqueous sodium chloride solution method until the crystals showed constant weight (about 80 hours). In this manner, the crystals of irinotecan hydrochloride were obtained.

Workup

dissolutiondissolved
additionby adding
customTo each mixture solution, 1 mg of c-type crystals separately prepared
additionwas added
customThe formed crystals were obtained by filtration
customdried under reduced pressure
customweight (about 80 hours)

Sources & evidence

ORD record: ord-eda3c6602abe47ebbcf0f0ec640f3d21
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488825B2

Reaction notes

Loading…