Water → Carbamic acid,[3-[(4-chloro-2,3-dihydro-7-iodo-1-oxo-1h-isoindol-5-yl)oxy]propyl]-,1,1-dimethylethyl ester

HRID 21321

Reaction equation

HRID 21321 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][CH2:29]Br)([CH3:23])([CH3:22])[CH3:21].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[C:10]([O:11][CH2:29][CH2:28][CH2:27][NH:26][C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:31])=[CH:9][C:8]([I:12])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 684892494-Chloro-5-hydroxy-7-iodoisoindolinone

Product 1

HCID 68489177Carbamic acid,[3-[(4-chloro-2,3-dihydro-7-iodo-1-oxo-1h-isoindol-5-yl)oxy]propyl]-,1,1-dimethylethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 429, 4-chloro-5-hydroxy-7-iodoisoindolinone (283 mg, 0.916 mmol) was dissolved in DMF (8.4 mL), and the solution was treated with potassium carbonate (190 mg, 1.37 mmol), tetrabutylammonium iodide (33.8 mg, 0.092 mmol) and 3-bromopropylcarbamic acid tert-butyl ester (654 mg, 2.75 mmol). The reaction mixture was added with water. The obtained solid was collected by filtration and purified by slurry using hexane and diisopropylether to obtain 4-chloro-5-[3-(tert-butoxycarbonylamino)propoxy]-7-iodoisoindolinone (350 mg, yield 84%).

Workup

  1. filtrationThe obtained solid was collected by filtration
  2. custompurified by slurry

Sources & evidence

ORD record
ord-645be3c128634fa1a7d8c21f5ccb0b87
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Linked notes

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