Sodium Bicarbonate → HCID 131721333, compound

HRID 1585100Notes

Reaction equation

HRID 1585100 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]=1[C@:19]1([O:37][C@H:36]([C:38]([O:40][CH3:41])=[O:39])[C@@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:21]1[O:22][C:23](=[O:25])[CH3:24])[OH:20])C)(OC(C)(C)C)=O.C(=O)(O)[O-].[Na+]>Cl.C(OCC)(=O)C>[CH3:1][NH:8][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[C@:19]1([O:37][C@H:36]([C:38]([O:40][CH3:41])=[O:39])[C@@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:21]1[O:22][C:23](=[O:25])[CH3:24])[OH:20]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 131721332HCID 131721332, compound

Product 1

HCID 131721333HCID 131721333, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-(N-BOC,N-methylamino)-4-nitrophenyl-2,3,4-tri-O-acetyl-β-D-glucuronate (5) (3 g, 5.13 mmol) in 2.12 M hydrochloric acid in ethyl acetate (60 ml) was stirred at room temperature for 1 hour. The solution was added to excess, aqueous, saturated sodium bicarbonate solution and the mixture was extracted with ethyl acetate. The organic phase was dried with sodium sulfate and concentrated. The product was chromatographed on silica gel (eluent dichloromethane/methanol 97.5/2.5). Yield 2.14 g (86%), yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. concentrationconcentrated
  4. customThe product was chromatographed on silica gel (eluent dichloromethane/methanol 97.5/2.5)

Sources & evidence

ORD record
ord-e96bc07700ef4087a58847d71165cf1f
Source dataset
uspto-grants-1999_08
Patent number
US05935995

Reaction notes

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