Ethanol → HCID 18608589, compound

HRID 2118713Notes

Reaction equation

HRID 2118713 reaction equation
[C:1]([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]1O)(=[O:3])[CH3:2].O.[CH2:17]([NH2:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[CH2:30]([OH:32])[CH3:31]>ClCCl>[CH2:17]([N:29]([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[NH:4][C:1](=[O:3])[CH3:2])[C:30](=[O:32])[CH2:31][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 13583DodecylamineHCID 439174N-Acetyl-D-Glucosamine

Product 1

HCID 18608589HCID 18608589, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

26 g of N-acetylglucosamine are dissolved in 100 ml of ethanol and 60 ml of water and the solution is heated to 60°. 37 g of dodecylamine are added and the mixture is stirred until a clear solution appears. After cooling to room temperature, the glycosylamine crystallizes out. The mass of crystals is filtered off with suction, washed with ethanol and then with ether and dried in vacuo. 3 g of the solid are suspended in 50 ml of tetrahydrofuran, 3.3 g of sodium carbonate are added and 1.9 g of tetradecanoyl chloride in 10 ml of tetrahydrofuran are added. After reaction is complete, the mixture is diluted with 30 ml of dichloromethane, filtered and the filtrate is evaporated in vacuo. The resulting syrup is purified by chromatography (mobile phase dichloromethane/methanol 20/1, (v/v)).

Workup

  1. customthe glycosylamine crystallizes out
  2. filtrationThe mass of crystals is filtered off with suction
  3. washwashed with ethanol
  4. dry with materialwith ether and dried in vacuo
  5. addition3.3 g of sodium carbonate are added
  6. addition1.9 g of tetradecanoyl chloride in 10 ml of tetrahydrofuran are added
  7. customAfter reaction
  8. filtrationfiltered
  9. customthe filtrate is evaporated in vacuo
  10. customThe resulting syrup is purified by chromatography (mobile phase dichloromethane/methanol 20/1, (v/v))

Sources & evidence

ORD record
ord-80721919d0da4220a5a661f991dcf471
Source dataset
uspto-grants-1987_07
Patent number
US04680287

Reaction notes

Loading…