Triethylamine → HCID 178524276, compound

HRID 1417147Notes

Reaction equation

HRID 1417147 reaction equation
[CH:1]1[C:6](N=C=S)=[CH:5][C:4]2[C:10]([O:12][C:13]3([C:23]4[CH:24]=[CH:25][C:26]([OH:28])=[CH:27][C:22]=4[O:21][C:15]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]3=4)[C:3]=2[CH:2]=1)=[O:11].NC1C=C([B:36]([OH:38])[OH:37])C=CC=1.C(N(CC)CC)C>CO>[CH:1]1[CH:6]=[CH:5][C:4]([C:10]([OH:12])=[O:11])=[C:3]([C:13]2[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[O:21][C:22]3[C:23]=2[CH:24]=[CH:25][C:26]([CH:27]=3)=[O:28])[CH:2]=1.[BH:36]([OH:38])[OH:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18730Fluorescein 5-isothiocyanateHCID 922693-Aminophenylboronic acid

Product 1

HCID 178524276HCID 178524276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A fluorescein-boronic acid compound of formula I above was prepared by the following method. Fluorescein isothiocyanate (10 mg), m-aminophenylboronic acid (4 mg) and triethylamine (3 mg) were mixed in 0.9 ml methanol, and 0.1 ml distilled water. The mixture was stirred for one hour at room temperature and then a further 4 mg of m-aminophenyl-boronic acid was added. Stirring was continued for a further hour, and the solution was then purified by thin layer chromatography (eluent dichloromethane:methanol, 9:1).

Workup

  1. distillation0.1 ml distilled water
  2. additiona further 4 mg of m-aminophenyl-boronic acid was added
  3. stirringStirring
  4. waitwas continued for a further hour
  5. customthe solution was then purified by thin layer chromatography (eluent dichloromethane:methanol, 9:1)

Sources & evidence

ORD record
ord-49e464453568452083f3f0d3cd441679
Source dataset
uspto-grants-1999_03
Patent number
US05877025

Reaction notes

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