1,2-Dichloroethane → 4-Hydroxyphenylacetic acid succinimidyl ester

HRID 1168201Notes

Reaction equation

HRID 1168201 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.O[N:27]1[C:31](=[O:32])[CH2:30][CH2:29][C:28]1=[O:33]>CN(C=O)C.C(OCC)(=O)C>[C:28]1(=[O:33])[N:27]([O:10][C:9](=[O:11])[CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[C:31](=[O:32])[CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 127Hydroxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 80170N-Hydroxysuccinimide

Product 1

HCID 235146144-Hydroxyphenylacetic acid succinimidyl esterYield 78.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-hydroxyphenylacetic acid (3.0 g, 20 mmol) in DMF was added HOBT (3.7 g, 24 mmol) followed by EDC (4.2 g, 22 mmol) and the mixture was stirred at room temperature for 30 min. N-hydroxysuccinimide (2.3 g, 20 mmol) was added and stirred at room temperature overnight. The resulting mixture was diluted with ethyl acetate (150 ml), extracted with 5% citric acid (2×), saturated NaHCO3 (2×) and brine (1×) and was dried over anhydrous Na2SO4. Following removal of the solvent in vacuo the product was dissolved in CH2Cl2 and precipitated with hexanes to afford 4-hydroxyphenylacetic acid succinimidyl ester (3.9 g, 78%). 1H NMR (300 MHz, DMSO-d6): 2.79 (s, 4H), 3.93 (s, 2H), 6.72 (d, J=8.5 Hz, 2H), 7.12 (d, J=8.5 Hz, 2H), 9.41 (s, 1H).

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with 5% citric acid (2×), saturated NaHCO3 (2×) and brine (1×)
  3. dry with materialwas dried over anhydrous Na2SO4
  4. customremoval of the solvent in vacuo the product
  5. dissolutionwas dissolved in CH2Cl2
  6. customprecipitated with hexanes

Sources & evidence

ORD record
ord-62c03853f5ec487290f70f0829580a29
Source dataset
uspto-grants-2003_09
Patent number
US06624152B2

Reaction notes

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