Octadecylamine → N-octadecylglucopyranosylamine

HRID 255870Notes

Reaction equation

HRID 255870 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

Procedure

20 g of octadecylamine are dissolved in 120 ml of ethanol and the solution is warmed to 70°. 11 g of anhydrous D-glucose are added. After a clear solution has formed, stirring is continued at 70° for a further 15 minutes. The mixture is cooled to 10° 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. temperaturethe solution is warmed to 70°
  2. customAfter a clear solution has formed
  3. temperatureThe mixture is cooled to 10°
  4. waitleft
  5. waitto stand for 15 minutes
  6. customThe crystal sludge formed
  7. filtrationis filtered off with suction
  8. washwashed twice with ethanol
  9. customdried in vacuo

Sources & evidence

ORD record
ord-ace6689b51774ea4845b266b7e04c7b7
Source dataset
uspto-grants-1987_10
Patent number
US04699899

Reaction notes

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