Hydrochloric Acid → 6-[4-[4-(9-Carboxy-9H-fluoren-9-yl) butyl]piperazin-1-yl]-2-cyclohexyl-2,3-dihydro-1H-isoindol-1-one

HRID 1836838Notes

Reaction equation

[CH:1]1([N:7]2[CH2:15][C:14]3[C:9](=[CH:10][C:11]([N:16]4[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]5([C:39]([O:41]CC)=[O:40])[C:38]6[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=6[C:32]6[C:27]5=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH2:18][CH2:17]4)=[CH:12][CH:13]=3)[C:8]2=[O:44])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[OH-].[Na+].Cl>CO>[C:39]([C:26]1([CH2:25][CH2:24][CH2:23][CH2:22][N:19]2[CH2:20][CH2:21][N:16]([C:11]3[CH:10]=[C:9]4[C:14]([CH2:15][N:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)[C:8]4=[O:44])=[CH:13][CH:12]=3)[CH2:17][CH2:18]2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=2[C:33]2[C:38]1=[CH:37][CH:36]=[CH:35][CH:34]=2)([OH:41])=[O:40]

Participants

Conditions

Temperature: 65 °C

Procedure

The compound (50 mg) prepared in Example 129 was dissolved in a mixed solvent composed of THF (0.3 ml) and methanol (0.3 ml). 1 N NaOH (0.3 ml) was added to the solution, and the mixture was heated at 65° C. with stirring for 3 hr. The temperature of the reaction solution was returned to room temperature, and 1 N HCl was then added thereto, followed by extraction with chloroform. The extract was dried over anhydrous MgSO4. The solvent was then removed by distillation under the reduced pressure. The residue was purified by preparative TLC (chloroform:methanol=5:1) to give the title compound (29 mg).

Workup

customwas returned to room temperature
extractionfollowed by extraction with chloroform
dry with materialThe extract was dried over anhydrous MgSO4
customThe solvent was then removed by distillation under the reduced pressure
customThe residue was purified by preparative TLC (chloroform:methanol=5:1)

Sources & evidence

ORD record: ord-f6e719b51b904ca89bb062ba399084f3
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777414B1

Reaction notes

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