Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Dodecylamine | HCID 13583 | — |
| Reactant | N-Acetyl-D-Glucosamine | HCID 439174 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 18608589 | HCID 18608589 | — |
Reaction Steps
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)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04680287 |
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| Source dataset | uspto-grants-1987_07 |
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| ORD ID | ord-80721919d0da4220a5a661f991dcf471 |
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| Source note | uspto-grants-1987_07 |
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