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 1836838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836838
[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]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 221803422-Cyclohexyl-6-[4-[4-(9-ethoxycarbonyl-9H-fluoren-9-yl)-butyl]piperazin-1-yl]-2,3-dihydro-1H-isoindol-1-one

Produkt 1

HCID 221806496-[4-[4-(9-Carboxy-9H-fluoren-9-yl) butyl]piperazin-1-yl]-2-cyclohexyl-2,3-dihydro-1H-isoindol-1-oneAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f6e719b51b904ca89bb062ba399084f3
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777414B1

Notizen zur Reaktion

Wird geladen…