Acetic Anhydride → HCID 178476371, compound

HRID 991153Notes

Reaction equation

HRID 991153 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:28])[C:7](=[C:14]([NH:16][C@@H:17]1[C@@H:23]([OH:24])[C@H:22]([OH:25])[C@@H:21]([CH2:26][OH:27])[O:20][CH:18]1[OH:19])[CH3:15])[C:8]2=[O:13])([O-:3])=[O:2].C(O[C:33](=[O:35])[CH3:34])(=O)C>N1C=CC=CC=1>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:28])[C:7](=[C:14]([NH:16][C@@H:17]1[C@@H:23]([O:24][C:8](=[O:13])[CH3:7])[C@H:22]([O:25][C:18](=[O:19])[CH3:17])[C@@H:21]([CH2:26][O:27][C:33](=[O:35])[CH3:34])[O:20][C@@H:18]1[OH:19])[CH3:15])[C:8]2=[O:13])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178464541HCID 178464541, compound

Product 1

HCID 178476371HCID 178476371, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-Deoxy-2-[1-(4-nitro-1,3-dioxoindan-2-ylidene)ethylamino]-D-glucopyranose (100 mg, 0.23 mmol), pyridine (2 ml) and acetic anhydride (3 ml) stirred at room temperature overnight. The reaction mixture was evaporated, and the residue was purified by chromatography using CHCl3/EtOAc 10:4 as the mobile phase to give 2-Deoxy-2-[1-(4-nitro-1,3-dioxoindan-2-ylidene)-ethylamino]-3,4,6-tri-O-acetyl-α-D-glucopyranose (23) (165 mg, 79%).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-bde6474b8dbe4ee692e3d5d5ccce45e1
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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