2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate → Theophylline

HRID 1684483Notes

Reaction equation

HRID 1684483 reaction equation
[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.N[CH2:22][N:23]1[C:33](=[O:34])[C:32]2[NH:31][CH:30]=[N:29][C:28]=2[N:26]([CH3:27])[C:24]1=[O:25]>O.B([O-])([O-])[O-]>[N:23]1([C:33](=[O:34])[C:32]2[NH:31][CH:30]=[N:29][C:28]=2[N:26]([CH3:27])[C:24]1=[O:25])[CH3:22]

Participants

5

Reactant 2

HCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 86750987HCID 86750987, compound2×

Product 1

HCID 2153Theophylline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 26574BorateSolvent

Procedure

The dye I (1,1'-(4-sulfobutyl)-3,3,3',3'-tetramethyl-6-carboxymethylindotricarbocyanine) was synthesized according to P. L. Southwick et al., Cytometry, 11 (1990) 418, dye XVIII. This dye is a water-soluble and reactive derivative of the dye HITC used in the previous examples. The absorption maximum in water was at 746 nm. The dye I was activated with TSTU (O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, Fluka, Switzerland) and dissolved in borate buffer (pH 8.5, 0.1M borate) containing aminotheophylline (8-(3-aminopropyl)theophylline). The reaction yielded a clear solution. Thin layer chromatography confirmed that the aminotheophylline was completely used up. The absorption spectrum of the reaction mixture was similar to that of pure dye I. In subsequent experiments, the reaction mixture was used without further purification.

Workup

  1. customThe dye I (1,1'-(4-sulfobutyl)-3,3,3',3'-tetramethyl-6-carboxymethylindotricarbocyanine) was synthesized
  2. customThe reaction yielded a clear solution
  3. customIn subsequent experiments, the reaction mixture was used without further purification

Sources & evidence

ORD record
ord-835a6aa88a9a4bbdaca0566f7c98381b
Source dataset
uspto-grants-1997_06
Patent number
US05641640

Reaction notes

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