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

HRID 1525812Notes

Reaction equation

HRID 1525812 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 was 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 was 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-3b0ff3e8afa44025973b9ab81a34d13a
Source dataset
uspto-grants-2015_07
Patent number
US09085563B2

Reaction notes

Loading…