Octadecylamine → N-octadecylglucopyranosylamine

HRID 1788899Notes

Reaction equation

HRID 1788899 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[O:20]=[CH:21][C@@H:22]([C@H:24]([C@@H:26]([C@@H:28]([CH2:30][OH:31])[OH:29])[OH:27])[OH:25])O>C(O)C>[CH2:1]([NH:19][CH:30]1[O:31][C@H:22]([CH2:21][OH:20])[C@@H:24]([OH:25])[C@H:26]([OH:27])[C@H:28]1[OH:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 15793OctadecylamineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 13361749N-octadecylglucopyranosylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

20 g of octadecylamine are dissolved in 120 ml of ethanol and the solution is warmed to 70° C. 11 g of anhydrous D-glucose are added. After a clear solution has formed, stirring is continued at 70° C. for a further 15 minutes. The solution is cooled to 10° C. and left to stand for 15 minutes. The crystal sludge formed is filtered off with suction, washed twice with ethanol and dried in vacuo.

Workup

  1. customAfter a clear solution has formed
  2. temperatureThe solution is cooled to 10° C.
  3. waitleft
  4. waitto stand for 15 minutes
  5. customThe crystal sludge formed
  6. filtrationis filtered off with suction
  7. washwashed twice with ethanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-938dad52bf424847b5a87b0af4a64a9c
Source dataset
uspto-grants-1987_08
Patent number
US04686208

Reaction notes

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