Bromoacetic Acid → 2-(1-(2-Hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione bromoacetate

HRID 475028Notes

Reaction equation

HRID 475028 reaction equation
[Br:1][CH2:2][C:3]([OH:5])=[O:4].[OH:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[C:10]1=[O:27].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[Br:1][CH2:2][C:3]([OH:5])=[O:4].[OH:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[CH2:13][CH2:12][CH:11]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[C:10]1=[O:27]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 119652712-(1-(2-Hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Product 1

HCID 866187532-(1-(2-Hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione bromoacetateYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromoacetic acid (138.95 mg) and 2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (288 mg) were dissolved in DCM (20 mL). The mixture was stirred on a magnetic stirrer at room temperature. DCC (206 mg) was added in one portion. The mixture was allowed to react overnight. Then, the mixture was filtered to remove dicyclohexylurea. The filter cake washed several times with DCM. The filtrates were combined and then washed three times with brine (30 mL/wash), dried over anhydrous magnesium sulfate, and filtered. The solvent was eliminated by rotary evaporation in vacuo and then white solid (390 mg) was obtained. 1H NMR (CDCl3, ppm) δ 7.88-7.90 (m, 2H), 7.77-7.79 (m, 2H), 4.96-5.08 (m, 1H), 4.85 (s, 2H), 4.02-4.12 (m, 2H), 3.76-3.80 (m, 2H), 2.94-3.02 (m, 1H), 2.72-2.90 (m, 2H), 2.14-2.23 (m, 1H).

Workup

  1. customto react overnight
  2. filtrationThen, the mixture was filtered
  3. customto remove dicyclohexylurea
  4. washThe filter cake washed several times with DCM
  5. washwashed three times with brine (30 mL/wash)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was eliminated by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-750c302da9ad4e869b852aece9bf021f
Source dataset
uspto-grants-2014_01
Patent number
US08637545B2

Reaction notes

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