Triethylamine → Triethylene Glycol

HRID 1795755Notes

Reaction equation

HRID 1795755 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:17])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16].C(O)(=O)CCCCCCC/C=C\CCCCCCCC>CS(C)=O>[CH2:8]([OH:17])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86759976HCID 86759976, compound

Product 1

HCID 8172Triethylene Glycol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Insulin (1.503 g, 0.26 mmoles) was weighed in a round bottom flask equipped with a stir bar. While stirring, DMSO (5 ml) was carefully added and allowed to stir until dissolved. Triethylamine (2.08 mmoles) was added and stirred for 10 minutes. Activated oleate triethylene glycol in minimum amount of DMSO (2 ml) was added carefully all at once and stirred for 3 h at room temperature. The reaction was monitored via HPLC every 30 mins. The conjugate was purified using a preparative HPLC.

Workup

  1. customInsulin (1.503 g, 0.26 mmoles) was weighed in a round bottom flask
  2. customequipped with a stir bar
  3. stirringto stir
  4. dissolutionuntil dissolved
  5. stirringstirred for 10 minutes
  6. stirringstirred for 3 h at room temperature
  7. customThe conjugate was purified

Sources & evidence

ORD record
ord-3c1ba07106ba4ddea0bac7983a0132aa
Source dataset
uspto-grants-2006_04
Patent number
US07030084B2

Reaction notes

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