Nitroxyl → HCID 90958724, compound

HRID 604404Notes

Reaction equation

HRID 604404 reaction equation
[CH:1]1[C:6](CCCC(O)=O)=[CH:5][CH:4]=[C:3]([N:13]([CH2:17][CH2:18][Cl:19])[CH2:14][CH2:15][Cl:16])[CH:2]=1.[CH3:20][C:21]1([CH3:31])[N:26]([O])[C:25]([CH3:29])([CH3:28])[CH2:24][CH:23](O)[CH2:22]1.N=[O:33].C(O)[C@@H](O)[C@H:36]1[O:41][C:39](=[O:40])[C:38](O)=[C:37]1O>C(O)C.O>[C:39]([O:41][C:6]1[CH:1]=[CH:2][C:3]([N:13]([CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][Cl:19])=[CH:4][C:5]=1[CH:23]1[CH2:22][C:21]([CH3:31])([CH3:20])[N:26]([OH:33])[C:25]([CH3:29])([CH3:28])[CH2:24]1)(=[O:40])[CH2:38][CH2:37][CH3:36]

Participants

6

Reactant 3

HCID 945NitroxylHCID 54675810Erythorbic AcidHCID 178426856HCID 178426856, compound

Product 1

HCID 90958724HCID 90958724, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In order to characterize the structure of the chlorambucil-TEMPOL adduct by using NMR spectroscopy, the nitroxyl free radical was reduced using isoascorbic acid. 3.4 mmol of the product was dissolved in 15 ml of ethanol and 4.8 mmol of isoascorbic dissolved in 1 ml H2O was then added to the solution. Reduction of the nitroxyl group to the hydroxyl was monitored by the disappearance of the pink color in the solution. The solution was then Rotovapped to remove excess solvent and extracted with ether. The organic phase was dried over MgSO4 and evaporated to get the reduced product (1-hydroxy2, 2, 6, 6-tetramethylpiperidin-4-yl-{4-[bis (2-Chloroethyl) amino] phenyl} butanoate) with 95% yield. The reduction of nitroxyl radical is illustrated as follows:

Workup

  1. additionwas then added to the solution
  2. customRotovapped to remove excess solvent
  3. extractionextracted with ether
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-5f1d20cb91b242e3b3f9279f176c3843
Source dataset
uspto-grants-2011_03
Patent number
US07910607B2

Reaction notes

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