Triethylamine → HCID 21881058, compound

HRID 724513Notes

Reaction equation

HRID 724513 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:53])[N:34]([CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH2:47][CH2:48][C:49](O)=[O:50])[C:33](=[O:52])[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:28]=[CH:29][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:10])[CH2:12][CH:13]([C:49](=[O:50])[CH2:48][CH2:47][O:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41][O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][N:34]3[C:30](=[O:53])[CH:31]=[CH:32][C:33]3=[O:52])[CH2:14]2)=[O:17])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21881060HCID 21881060, compoundHCID 21881063HCID 21881063, compound

Product 1

HCID 21881058HCID 21881058, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of PMB-CB-OH (1.154 g, 2.881 mmol), 15-maleinimido-4,7,10,13-tetroxapentadecanoic acid (1.49 g, 4.32 mmol) and triethylamine (1.20 ml, 8.64 mmol) in 20 ml anhydrous dichloromethane is admixed with 2-chloro-1-methylpyridinium iodide (1.10 g, 4.32 mmol) and stirred for three hours at room temperature. It is diluted with 80 ml dichloromethane, washed each time twice with 50 ml 1 n hydrochloric acid, 50 ml water and once with 50 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, ethyl acetate). 1.93 g PMB-CB-4-Mal (92% of theory) is obtained as a colourless oil.

Workup

  1. washwashed each time twice with 50 ml 1 n hydrochloric acid, 50 ml water
  2. dry with materialonce with 50 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, ethyl acetate)
  5. custom1.93 g PMB-CB-4-Mal (92% of theory) is obtained as a colourless oil

Sources & evidence

ORD record
ord-225e558d85db4fe5a48a8a59d5cc9972
Source dataset
uspto-grants-2006_11
Patent number
US07141691B2

Reaction notes

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