Triethylamine → m-PEG4-succinimidyl carbonate

HRID 513878

Reaction equation

HRID 513878 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13]O.C1C(=O)N([O:22][C:23]([O:25][N:26]2[C:31](=[O:32])[CH2:30][CH2:29][C:27]2=[O:28])=[O:24])C(=O)C1.C(N(CC)CC)C.C(OCC)(=O)C.CO>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:22][C:23](=[O:24])[O:25][N:26]1[C:27](=[O:28])[CH2:29][CH2:30][C:31]1=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90263Tetraethylene glycol monomethyl etherHCID 676246Di(succinimido) carbonateHCID 21584119Ethylacetate methanol

Product 1

HCID 59659904m-PEG4-succinimidyl carbonateYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tetraethylene glycol monomethyl ether (1.0 g, 4.8 mmol) and N,N′-disuccinimidyl carbonate (1.48 g, 5.8 mmol) were dissolved in acetonitrile (10 mL). Then triethylamine (1.0 mL, 7.2 mmol) was added and the reaction stirred overnight at room temperature. Crude reaction was evaporated to dryness, dissolved in sat. NaHCO3 (30 mL), washed ethyl acetate (2×30 mL), dried MgSO4, and evaporated to dryness. Column chromatography (Silica, ethyl acetate/MeOH, 20:1) afforded 1 a clear oil (0.462 g, 28% yield).

Workup

  1. customCrude reaction
  2. customwas evaporated to dryness
  3. dissolutiondissolved in sat. NaHCO3 (30 mL)
  4. washwashed ethyl acetate (2×30 mL), dried MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b3e9539dee4241a190a4ffc0e7def378
Source dataset
uspto-grants-2015_08
Patent number
US09102758B2

Linked notes

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