Acetic Anhydride → 4-Acetamidophenyl 4-O-(alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

HRID 2417865Notes

Reaction equation

HRID 2417865 reaction equation
[C@H:1]1([O:12][C@@H:13]2[C@@H:26]([CH2:27][OH:28])[O:25][C@@H:16]([S:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)[C@H:15]([OH:29])[C@H:14]2[OH:30])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[C:31](OC(=O)C)(=[O:33])[CH3:32]>O>[C@H:1]1([O:12][C@@H:13]2[C@@H:26]([CH2:27][OH:28])[O:25][C@@H:16]([S:17][C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:31](=[O:33])[CH3:32])=[CH:22][CH:23]=3)[C@H:15]([OH:29])[C@H:14]2[OH:30])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 542687654-aminophenyl 4-O-(alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

Product 1

HCID 545032914-Acetamidophenyl 4-O-(alpha-D-glucopyranosyl)-1-thio-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1.0 g portion of 4-aminophenyl 4-O-(α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside was dissolved in 5 ml of water and 0.340 ml of acetic anhydride was added with vigorous stirring. After stirring 10 minutes the reaction was concentrated, reconcentrated from toluene, dissolved in ethanol and precipitated with ether, giving 836 mg of the desired intermediate.

Workup

  1. concentrationwas concentrated
  2. dissolutiondissolved in ethanol
  3. customprecipitated with ether

Sources & evidence

ORD record
ord-e85e80f0027a42138dfdf20e37984306
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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