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

HRID 21264Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 50 °C

Procedure

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%).

Workup

filtrationThe precipitated solid was collected by filtration
washwashed with water
customby drying under reduced pressure

Sources & evidence

ORD record: ord-bee2520953484577908e40344c0aa73f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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