Benzoyl Peroxide → HCID 86755268, compound

HRID 1638147Notes

Reaction equation

HRID 1638147 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[N+:27]([C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:31]=1[C@:37]1([O:55][C@H:54]([C:56]([O:58][CH3:59])=[O:57])[C@@H:49]([O:50][C:51](=[O:53])[CH3:52])[C@H:44]([O:45][C:46](=[O:48])[CH3:47])[C@H:39]1[O:40][C:41](=[O:43])[CH3:42])[OH:38])([O-:29])=[O:28]>C(Cl)(Cl)(Cl)Cl>[N+:27]([C:30]1[CH2:35][C:34](=[CH:36][Br:1])[CH:33]=[CH:32][C:31]=1[C@:37]1([O:55][C@H:54]([C:56]([O:58][CH3:59])=[O:57])[C@@H:49]([O:50][C:51](=[O:53])[CH3:52])[C@H:44]([O:45][C:46](=[O:48])[CH3:47])[C@H:39]1[O:40][C:41](=[O:43])[CH3:42])[OH:38])([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53907025HCID 53907025, compound

Product 1

HCID 86755268HCID 86755268, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (117.2 mg, 0.66 mmol) and benzoyl peroxide (159 mg, 0.66 mmol) were added to a solution of methyl 1-(2-nitro-4-methylphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate (206 mg, 0.44 mmol) in carbon tetrachloride (20 ml). The mixture was refluxed for 5 hours and stirred at room temperature for 12 hours. The reaction mixture was evaporated under reduced pressure, and purified by column chromatography on silica gel (ethyl acetate-hexane, 2:3) to give 47 mg of methyl 1-(2-nitro-4-bromomethylene-phenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate in 20% yield. 1H NMR (300 MHz, DMSO-d6) δ1.98-2.02 (m, 9H, CH3), 3.64 (s, 3H, OCH3), 4.73 (s, 2H, CH2), 4.77 (s, 1H, sugar-H), 5.09-5.13 (m, 2H, sugar-H), 5.47 (t, J=9 Hz, 1H, sugar-H), 5.76 (d, J=7.7 Hz, 1H, sugar-H), 7.43 (d, J=8.7 Hz, 1H, ArH), 7.76 (d, J=8.7 Hz, 1H, ArH), 8.02 (s, 1H, ArH).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. custompurified by column chromatography on silica gel (ethyl acetate-hexane, 2:3)

Sources & evidence

ORD record
ord-6d962a8521ab4abe978e2755e80c0535
Source dataset
uspto-grants-2000_03
Patent number
US06043367

Reaction notes

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