Acetic Anhydride → HCID 23453194, compound

HRID 1277684Notes

Reaction equation

HRID 1277684 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH2:9][C:10]1([CH2:19][OH:20])[CH:15]([OH:16])[CH:14]([OH:17])[CH:13]([OH:18])[CH2:12][NH:11]1>CO.O>[C:1]([NH:8][CH2:9][C:10]1([CH2:19][OH:20])[CH:15]([OH:16])[CH:14]([OH:17])[CH:13]([OH:18])[CH2:12][NH:11]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 20449507HCID 20449507, compound

Product 1

HCID 23453194HCID 23453194, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

5.1 ml of acetic anhydride are added to a solution of 6.5 g of crude 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxy-piperidine in 65 ml of methanol/water (1:1) at 0° C. The mixture is stirred at 0° C. for 30 minutes and at room temperature for 18 hours. The solution is concentrated in vacuo, the residue is dissolved in a little water and, to remove the acetic acid formed, the solution is filtered through an anion exchanger in the OH⃝ form and the column is washed with water. The filtrate is concentrated, the residue is dissolved in a little water and the solution is discharged onto a cellulose column 120 cm long and 3 cm wide which contains butanol as the mobile phase. The column is eluted with butanol, 95% pure butanol and 90% pure butanol and the individual fractions are investigated by thin layer chromatography to determine their content of the required compound. The fractions containing the desired product are collected and concentrated. The residue is dissolved in hot methanol and the solution is filtered and concentrated down to a volume of 30 ml. The product crystallises out. The crystallisation is brought to completion by leaving the mixture to stand overnight. The product is filtered off and washed with methanol. 2.7 g of colourless crystals of melting point 196° C. (decomposition) are obtained.

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. dissolutionthe residue is dissolved in a little water
  3. customto remove the acetic acid
  4. customformed
  5. filtrationthe solution is filtered through an anion exchanger in the OH⃝ form
  6. washthe column is washed with water
  7. concentrationThe filtrate is concentrated
  8. dissolutionthe residue is dissolved in a little water
  9. washThe column is eluted with butanol, 95% pure butanol and 90% pure butanol
  10. additionThe fractions containing the desired product
  11. customare collected
  12. concentrationconcentrated
  13. dissolutionThe residue is dissolved in hot methanol
  14. filtrationthe solution is filtered
  15. concentrationconcentrated down to a volume of 30 ml
  16. customThe product crystallises out
  17. customThe crystallisation
  18. customby leaving the mixture
  19. waitto stand overnight
  20. filtrationThe product is filtered off
  21. washwashed with methanol

Sources & evidence

ORD record
ord-bb9d1f3be312449bba6f03dd322ed176
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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