Water → HCID 86628297, compound

HRID 21265Notes

Reaction equation

[CH3:1][S:2]([O:5][C:6]1[C:14]([CH:15](OC)[O:16][CH3:17])=[CH:13][C:12]([I:20])=[C:11]2[C:7]=1[CH:8](OC)[N:9](C(C)(C1C=CC=CC=1)C)[C:10]2=[O:21])(=[O:4])=[O:3].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>[N+](C)([O-])=O.CCCCCC.C(OCC)(=O)C>[CH3:1][S:2]([O:5][C:6]1[C:14]([CH2:15][O:16][CH3:17])=[CH:13][C:12]([I:20])=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:21])(=[O:3])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

In a similar manner to Step 4 of Example 16, 4-methanesulfonyloxy-5-dimethoxymethyl-3-methoxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (226 mg, 0.393 mmol) was dissolved in nitromethane (5 mL), and the solution was added with trifluoroacetic acid (0.775 mL, 10.1 mmol) and triethylsilane (0.406 mL, 2.51 mmol), followed by stirring at 50° C. for 1 hour. The reaction mixture was added with water, ethyl acetate and hexane. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-methanesulfonyloxy-5-methoxymethyl-7-iodoisoindolinone (113 mg, yield 72%).

Workup

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

Sources & evidence

ORD record: ord-576ef63e032743879434c13e7bc63fbb
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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