Dimethylformamide → Carbazole

HRID 2259538Notes

Reaction equation

HRID 2259538 reaction equation
CC1C(O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O[C@H]3O[C@H](C)[C@@H](O)[C@H](O)C3)C2)=C[C:5]2[C:10](C=1O)=[C:9](O)[C:8]1C([C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](O[C@H]4O[C@H](C)[C@H](O[C@H]5O[C@H](C)[C@@H](O)[C@](O)(C)C5)[C@H](O)C4)C3)[C@H:17]([C@H:19](OC)[C:20]([C@@H:22](O)[C@H:23](O)C)=O)[CH2:18][C:7]=1[CH:6]=2)=O.[OH-].[Na+].C[N:80](C)C=O>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].O>[CH:9]1[C:8]2[NH:80][C:17]3[C:18](=[CH:23][CH:22]=[CH:20][CH:19]=3)[C:7]=2[CH:6]=[CH:5][CH:10]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 52945526HCID 52945526, compound

Product 1

HCID 6854Carbazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24243Trisodium PhosphateSolvent

Procedure

Heparin adipic hydrazide (70 mg) was dissolved in 6 ml of 0.1M sodium phosphate buffer, pH 5.8. Mithramycin (10 mg) was dissolved in 1 ml dimethylformamide and this solution was mixed with the heparin adipic hydrazide solution and left for 21/2% days at room temperature. The reaction mixture was then applied to a column of Sephadex G25 equilibrated in H2O whose pH had been raised to approximately 10 by the addition of dilute NaOH. The conjugate, which elated in the void volume, was collected and freeze dried. Quantitation of the drug by u.v spectrophotometric analysis and of the heparin by carbazole assay gave the composition of the conjugate as 0.54 mol mithromycin:mol heparin. The conjugate (Table III) has the structure shown in FIG. 2.

Workup

  1. waitleft for 21/2% days at room temperature
  2. customwas collected
  3. customfreeze dried

Sources & evidence

ORD record
ord-8874f836520c4734a413080e4a6a6edf
Source dataset
uspto-grants-1995_12
Patent number
US05474765

Reaction notes

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