HCID 18391175, compound → HCID 131721332, compound

HRID 1585099Notes

Reaction equation

HRID 1585099 reaction equation
[C:1]([N:8]([C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1O)[CH3:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br-].[C:21]([O:24][C@@H:25]1[C@@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:30]([O:36][C:37](=[O:39])[CH3:38])[C@@H:29]([C:40]([O:42][CH3:43])=[O:41])[O:28][C@@H:26]1[OH:27])(=[O:23])[CH3:22]>C(#N)C.[Ag]=O>[C:1]([N:8]([C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[C@:26]1([O:28][C@H:29]([C:40]([O:42][CH3:43])=[O:41])[C@@H:30]([O:36][C:37](=[O:39])[CH3:38])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:25]1[O:24][C:21](=[O:23])[CH3:22])[OH:27])[CH3:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 18391175HCID 18391175, compoundHCID 21221757HCID 21221757, compound

Product 1

HCID 131721332HCID 131721332, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

Silver oxide (0.23 g, 0.992 mmol) and 2-(N-BOC,N-methylamino)-4-nitrophenol (3) were added to a solution of methyl 2,3,4-tri-O-acetyl-a-D-glucuronate bromide (4) (126 mg, 0.317 mmol) in acetonitrile (5 ml). The reaction mixture was stirred at room temperature for 1 hour, filtered through Celite and concentrated in vacuo. The product was chromatographed on silica gel (eluent dichloromethane/methanol 97.5/2.5). Yield 165 mg (89%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe product was chromatographed on silica gel (eluent dichloromethane/methanol 97.5/2.5)

Sources & evidence

ORD record
ord-080e326a1e284ac4a8e4ead567ff8ef1
Source dataset
uspto-grants-1999_08
Patent number
US05935995

Reaction notes

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