hydroxylamine-O-sulfonic acid → HCID 18173077, compound

HRID 395886Notes

Reaction equation

HRID 395886 reaction equation
[O:1]=[C:2]1[CH:7]2[CH:5]3[CH:6]2[CH2:8][CH:3]1[CH:4]3[C:9]1[NH:17][C:16]2[C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH3:21])[C:13](=[O:22])[N:12]([CH2:23][CH2:24][CH3:25])[C:11]=2[N:10]=1.[NH2:26]OS(O)(=O)=O.C([O-])(O)=O.[Na+]>CC(O)=O>[O:1]=[C:2]1[NH:26][CH:3]2[CH2:8][CH:6]3[CH:5]([CH:4]2[C:9]2[NH:17][C:16]4[C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH3:21])[C:13](=[O:22])[N:12]([CH2:23][CH2:24][CH3:25])[C:11]=4[N:10]=2)[CH:7]13

Participants

5

Reactant 3

HCID 76284hydroxylamine-O-sulfonic acidHCID 516892Sodium BicarbonateHCID 18173123HCID 18173123, compound

Product 1

HCID 18173077HCID 18173077, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8-(5-Oxo-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (150 mg) was taken in HOAc (5 ml) and H2NOSO3H (100 mg) was added and refluxed for 5 hrs. Cooled to room temperature, treated with ice, sat NaHCO3, extracted with ethyl acetate, washed with brine, and dried over MgSO4. After concentration, the crude product was crystallized from acetone/water. Yield (135 mg). Mass (ES+358).

Workup

  1. temperaturerefluxed for 5 hrs
  2. additiontreated with ice
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration
  7. customthe crude product was crystallized from acetone/water
  8. customYield (135 mg)

Sources & evidence

ORD record
ord-cef1eed6cf384151a824b38194230b20
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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