2-Hydroxyethyl acrylate → HCID 23576933, compound

HRID 1826570Notes

Reaction equation

HRID 1826570 reaction equation
O[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].[C:17]([O:21][CH2:22][CH2:23]O)(=[O:20])[CH:18]=[CH2:19].S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:17]([O:21][CH2:22][CH2:23][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)(=[O:20])[CH:18]=[CH2:19]

Participants

5

Reactant 3

HCID 131652-Hydroxyethyl acrylateHCID 24386Thionyl ChlorideHCID 171548Biotin2×

Product 1

HCID 23576933HCID 23576933, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At room temperature, 500 mg of biotin (Compound i, product of Merck & Co., Inc.), 200 mg of 2-hydroxyethyl acrylate, 20 ml of thionyl chloride and 20 ml of toluene were mixed. The resulting mixture was refluxed for 2 hours. The solvent was then distilled off under reduced pressure. The residue was subjected to column chromatography by using a chloroform-methanol solvent mixture. By removal of the solvent, 100 mg of 2-biotinylethyl acrylate (Compound A) was obtained as a powdery substance (yield: 14%).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. customBy removal of the solvent

Sources & evidence

ORD record
ord-37de1e9a997c4196acea327498de8e8b
Source dataset
uspto-grants-2006_05
Patent number
US07052917B1

Reaction notes

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