Water → 4-Methanesulfonyloxy-5-dimethoxymethyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 21264
[CH3:1][S:2]([O:5][C:6]1[C:14](C=O)=[CH:13][C:12]([I:17])=[C:11]2[C:7]=1[CH:8]([O:28][CH3:29])[N:9]([C:19]([CH3:27])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:20])[C:10]2=[O:18])(=[O:4])=[O:3].[CH:30]([O:35][CH3:36])([O:33][CH3:34])OC.C(=O)([O-])O.[Na+].O>CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][S:2]([O:5][C:6]1[C:14]([CH:30]([O:33][CH3:34])[O:35][CH3:36])=[CH:13][C:12]([I:17])=[C:11]2[C:7]=1[CH:8]([O:28][CH3:29])[N:9]([C:19]([CH3:20])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:27])[C:10]2=[O:18])(=[O:3])=[O:4]

Komponenten

7

Edukt 4

HCID 962WaterHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 86628294HCID 86628294, Verbindung

Produkt 1

HCID 866282964-Methanesulfonyloxy-5-dimethoxymethyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Methanesulfonyloxy-5-formyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (220 mg, 0.416 mmol) was dissolved in methanol (4 mL), and the solution was added with trimethyl orthoformate (0.091 mL, 0.83 mmol) and p-toluenesulfonic acid monohydrate (1.0 mg, 0.0058 mmol), followed by stirring at 50° C. for 5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and water. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-methanesulfonyloxy-5-dimethoxymethyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (231 mg, yield 96%).

Aufarbeitung

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customby drying under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bee2520953484577908e40344c0aa73f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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