Acetic Anhydride → N-Acetyl-D-Glucosamine

HRID 1840254Notes

Reaction equation

HRID 1840254 reaction equation
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[NH2:5].CO[Na].CO.[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:19]([NH:5][C@@H:4]1[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([CH2:12][OH:13])[O:11][CH:3]1[OH:2])(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideHCID 178501943HCID 178501943, compound

Product 1

HCID 439174N-Acetyl-D-Glucosamine

Procedure

D-glucosamine hydrochloride (100 g, 0.46 mol) is added to a 0.6M solution of MeONa/MeOH and stirred for 5 minutes. Acetic anhydride (48 ml) is then added, and after 30 minutes a white precipitate appears, which is filtered and washed with cold ethanol. The liquor is recrystallised from absolute ethanol, obtaining 79.3 g of the compound (quantitative).

Workup

  1. waitafter 30 minutes a white precipitate appears
  2. filtrationwhich is filtered
  3. washwashed with cold ethanol
  4. customThe liquor is recrystallised from absolute ethanol

Sources & evidence

ORD record
ord-992cad5c097e4ba7baeffa70f898ef4e
Source dataset
uspto-grants-2004_01
Patent number
US06680304B2

Reaction notes

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