Water → Diethyl [(tert-butoxycarbonyl)amino](3-iodobenzyl)malonate

HRID 1441965Notes

Reaction equation

HRID 1441965 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[C:10]([O:14][C:15]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].[H-].[Na+].O>CN(C=O)C>[C:10]([O:14][C:15]([NH:17][C:18]([CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([I:1])[CH:3]=1)([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonateHCID 27593613-Iodobenzyl bromide

Product 1

HCID 67189170Diethyl [(tert-butoxycarbonyl)amino](3-iodobenzyl)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25 g (84.2 mmol) of 3-iodobenzyl bromide are added to a solution of 24.3 g (88.4 mmol) of diethyl [(tert-butoxycarbonyl)amino]malonate and 3.7 g (92.6 mmol) of sodium hydride in 300 ml of DMF while cooling in ice. After stirring the mixture at RT for 4 h, 5 ml of water are added cautiously while cooling in ice. The mixture is extracted several times with ethyl acetate, and the combined organic phases are washed with a saturated sodium chloride solution and water, dried over magnesium sulfate and concentrated in vacuo. The crude product is dried under high vacuum.

Workup

  1. temperaturewhile cooling in ice
  2. temperaturewhile cooling in ice
  3. extractionThe mixture is extracted several times with ethyl acetate
  4. washthe combined organic phases are washed with a saturated sodium chloride solution and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. dry with materialThe crude product is dried under high vacuum

Sources & evidence

ORD record
ord-5ff108df3253464cabd92307a0b94970
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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