Triethylene glycol monomethyl ether → m-PEG3-succinimidyl carbonate

HRID 254610Notes

Reaction equation

HRID 254610 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-f5870de62f24478b9e709dd488459d74
Source dataset
uspto-grants-2011_01
Patent number
US07875700B2

Reaction notes

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