Triethylene glycol monomethyl ether → m-PEG3-succinimidyl carbonate

HRID 253675

Reaction equation

HRID 253675 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10]O.C1C(=O)N([O:19][C:20]([O:22][N:23]2[C:28](=[O:29])[CH2:27][CH2:26][C:24]2=[O:25])=[O:21])C(=O)C1.C(N(CC)CC)C.C(OCC)(=O)C>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:19][C:20](=[O:21])[O:22][N:23]1[C:24](=[O:25])[CH2:26][CH2:27][C:28]1=[O:29]

Participants

6

Reactant 4

HCID 8178Triethylene glycol monomethyl etherHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 676246Di(succinimido) carbonate

Product 1

HCID 51340961m-PEG3-succinimidyl carbonateYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylene glycol monomethyl ether (1.0 g, 6.1 mmol) and N,N′-disuccinimidyl carbonate (1.87 g, 7.3 mmol) were dissolved in acetonitrile (10 mL). Then triethylamine (1.3 mL, 9.15 mmol) was added and the reaction stirred overnight at room temperature. Crude reaction was evaporated to dryness, dissolved in sat. NaHCO3 (50 mL), washed ethyl acetate (2×50 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate) afforded 1 a clear oil (0.367 g, 20% yield).

Workup

  1. customCrude reaction
  2. customwas evaporated to dryness
  3. dissolutiondissolved in sat. NaHCO3 (50 mL)
  4. washwashed ethyl acetate (2×50 mL), dried MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d5888878d97f4e84adf39d093588766b
Source dataset
uspto-grants-2011_01
Patent number
US07872095B2

Linked notes

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