Triethylamine → HCID 21881064, compound

HRID 724512Notes

Reaction equation

HRID 724512 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]([C:11]2([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)=[O:17])[CH2:14][CH:13](O)[CH2:12]2)=[O:10])=[CH:5][CH:4]=1.[C:30]1(=[O:44])[N:34]([CH2:35][CH2:36][O:37][CH2:38][CH2:39][C:40](O)=[O:41])[C:33](=[O:43])[CH:32]=[CH:31]1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[CH3:27][O:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][C:16]([C:11]2([C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:29][CH:28]=3)=[O:10])[CH2:14][CH:13]([C:40](=[O:41])[CH2:39][CH2:38][O:37][CH2:36][CH2:35][N:34]3[C:30](=[O:44])[CH:31]=[CH:32][C:33]3=[O:43])[CH2:12]2)=[O:17])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21881060HCID 21881060, compoundHCID 21881065Mal-PEG1-acid

Product 1

HCID 21881064HCID 21881064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of PMB-CB-OH (1.97 g, 4.91 mmol), 6-maleinimido-4-oxacaproic acid (1.57 g, 7.37 mmol) and triethylamine (2.04 ml, 8.64 mmol) is admixed with 2-chloro-1-methylpyridinium iodide (1.88 g, 7.37 mmol) in 30 ml anhydrous dichloromethane and stirred for three hours at room temperature. It is diluted with 140 ml dichloromethane, washed each time twice with 80 ml in hydrochloric acid, 80 ml water and once each time with 80 ml sodium chloride solution (saturated) and dried over magnesium sulfate. Subsequently the solvent is removed in a vacuum and the residue is purified by column chromatography (silica gel, chloroform/methanol 200:1). 2.89 g PMB-CB-1-Mal (99% of theory) is obtained as a colourless oil.

Workup

  1. washwashed each time twice with 80 ml in hydrochloric acid
  2. dry with material80 ml water and once each time with 80 ml sodium chloride solution (saturated) and dried over magnesium sulfate
  3. customSubsequently the solvent is removed in a vacuum
  4. customthe residue is purified by column chromatography (silica gel, chloroform/methanol 200:1)
  5. custom2.89 g PMB-CB-1-Mal (99% of theory) is obtained as a colourless oil

Sources & evidence

ORD record
ord-ac9c726ad13140cc95022aeb4c1c7ef0
Source dataset
uspto-grants-2006_11
Patent number
US07141691B2

Reaction notes

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