Ethanol → HCID 18608589, compound

HRID 2119157Notes

Reaction equation

HRID 2119157 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 were dissolved in 100 ml of ethanol and 60 ml of water and heated to 60°. 37 g of dodecylamine were added and stirred until a clear solution was achieved. The glycosylamine crystallised out after cooling down to room temperature. The mass of crystals was filtered off with suction, washed with ethanol and then with ether and dried in vacuo. 3 g of the solid material were suspended in 50 ml of tetrahydrofuran, 3.3 g of sodium carbonate were added and 1.9 g of tetradecanoyl chloride in 10 ml of tetrahydrofuran were added. After completion of reaction, the mixture was diluted with 30 ml of dichloromethane, filtered and the filtrate was evaporated in vacuo. The syrup obtained was purified by chromatography (mobile phase dichloromethane/methanol 20/1, (v/v)).

Workup

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

Sources & evidence

ORD record
ord-511473b218e640a4a1b23cf8db7b6ca6
Source dataset
uspto-grants-1987_07
Patent number
US04683222

Reaction notes

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