Hydrochloric Acid → (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

HRID 1644158Notes

Reaction equation

HRID 1644158 reaction equation
C([NH:4][C@@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=O)C.[ClH:16]>O>[ClH:16].[OH:7][CH:6]1[O:8][C@H:9]([CH2:14][OH:15])[C@@H:10]([OH:13])[C@H:11]([OH:12])[C@H:5]1[NH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 439174N-Acetyl-D-Glucosamine2×

Product 1

HCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochlorideYield 161.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The apparatus for this test consisted of a 1 liter round bottom vessel heated with a heating mantel. The ingredients, 150 grams of water, 21 g of 98% N-acetylglucosamine and 238 grams of 36.7% hydrochloric acid, were mixed together and added to the reaction vessel. The stirred reaction mix was heated up to 70° C. and mixed for 3 hours at which time the mixture was transferred to a beaker and cooled to 20° C. Few crystals were present. The mixture was transferred back into the reaction vessel and 10 grams of N-acetylglucosamine added. The reactor was reheated to 70° C. and reacted for 3 hours, cooled to 4° C. overnight. The crystals present were filtered and washed with ethanol, vacuum dried and assayed (20 g of glucosamine hydrochloride at 99.9%). The filtrate was transferred back into the reaction vessel and 10 g of N-acetylglucosamine were added. The reactor was again heated to 70° C., reacted for 3 hours, cooled overnight to 4° C., filtered, ethanol washed, vacuum dried and assayed (16.1 g of glucosamine hydrochloride at 99.6%). The filtrate was again returned to the reactor, 41.5 grams added and the reaction cycle repeated. Thirty-three grams of glucosamine hydrochloride resulted from the 4th cycle with an assay of 99.5%. The total yield was 86% with all the glucosamine hydrochloride produced 99+ in assay and white in color. This material did not need recrystallization.

Workup

  1. customThe apparatus for this test consisted of a 1 liter round bottom vessel
  2. temperatureheated with a heating mantel
  3. additionadded to the reaction vessel
  4. customThe stirred reaction
  5. additionmix
  6. additionmixed for 3 hours at which time the mixture
  7. temperaturecooled to 20° C
  8. additionadded
  9. customwas reheated to 70° C.
  10. customreacted for 3 hours
  11. temperaturecooled to 4° C. overnight
  12. filtrationThe crystals present were filtered
  13. washwashed with ethanol, vacuum
  14. customdried
  15. additionwere added
  16. temperatureThe reactor was again heated to 70° C.
  17. customreacted for 3 hours
  18. temperaturecooled overnight to 4° C.
  19. filtrationfiltered
  20. washethanol washed
  21. customvacuum dried
  22. additionadded
  23. customthe reaction cycle

Sources & evidence

ORD record
ord-7929f852f55c45b0b538addab30bb838
Source dataset
uspto-grants-2012_02
Patent number
US08124381B2

Reaction notes

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