Triethylamine → Triethylene Glycol

HRID 1375931Notes

Reaction equation

HRID 1375931 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-cd2d7c25f50f4e9ba85eac76b691de00
Source dataset
uspto-grants-2007_01
Patent number
US07169889B1

Reaction notes

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