m-Chloroperbenzoic acid → HCID 178526287, compound

HRID 965184Notes

Reaction equation

HRID 965184 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[N:11]=[CH:12][N:13]([C:23]=2[N:24]=[CH:25][N:26]=1)[C@@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(O)(=O)C>[CH2:1]([NH:8][C:9]1[N+:26]([O-:35])=[CH:25][N:24]=[C:23]2[C:10]=1[N:11]=[CH:12][N:13]2[C@@H:14]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[C@H:15]1[OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 92208Adenosine, N-(phenylmethyl)-

Product 1

HCID 178526287HCID 178526287, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N6 -Benzyladenosine (25 mg, 70 μmol) and m-chloroperbenzoic acid (38 mg, 220 μmol) were dissolved in 1 ml acetic acid. The resulting solution was stirred at room temperature for 2 days. The solvent was evaporated under a stream of nitrogen, and the residue was dissolved in a minimum of methanol and chromatographed on a silica plate (250μ) using acetonitrile:water, 4:1 (v/v). The UV absorbing band at Rf =0.53 was extracted with methanol to provide 7.3 mg (28% yield) of N6 -benzyladenosine-N1 -oxide. Mass and 1H-NMR spectra were consistent with the assigned structure.

Workup

  1. customThe solvent was evaporated under a stream of nitrogen
  2. dissolutionthe residue was dissolved in a minimum of methanol
  3. customchromatographed on a silica plate (250μ)
  4. customThe UV absorbing band at Rf =0.53
  5. extractionwas extracted with methanol

Sources & evidence

ORD record
ord-98278d55c62d4d20a8eacc8550879a73
Source dataset
uspto-grants-1998_06
Patent number
US05773423

Reaction notes

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