Tetrahydrofuran → N-Octadecyl-N-(D-glucopyranosyl)-decylurethane

HRID 255873

Reaction equation

HRID 255873 reaction equation
[CH2:1]([NH:19][CH:20]1[O:28][C@H:27]([CH2:29][OH:30])[C@@H:25]([OH:26])[C@H:23]([OH:24])[C@H:21]1[OH:22])[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].[C:31](=[O:34])([O-])[O-:32].[Na+].[Na+].ClC(O[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=O.O1CC[CH2:53][CH2:52]1>C(O)C>[CH2:1]([N:19]([CH:20]1[O:28][C@H:27]([CH2:29][OH:30])[C@@H:25]([OH:26])[C@H:23]([OH:24])[C@H:21]1[OH:22])[C:31]([O:32][CH:49]([CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:52][CH3:53])[CH3:50])=[O:34])[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

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10340Sodium CarbonateHCID 108727Decyl chloroformateHCID 13361749N-octadecylglucopyranosylamine

Product 1

HCID 22837650N-Octadecyl-N-(D-glucopyranosyl)-decylurethane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9 g of the compound from Example 1 were suspended in 160 ml of tetrahydrofuran and 40 ml of ethanol, and 9 g of sodium carbonate were added. 5 g of decyl chloroformate, dissolved in 40 ml of tetrahydrofuran, are added dropwise to this suspension in the course of 20 minutes. When the reaction has ended, the batch is filtered and the residue on the filter is rinsed with tetrahydrofuran. The filtrate is combined with the wash solutions and evaporated in vacuo. The resulting syrup is purified by chromatography (mobile phase methylene chloride/methanol, 20:1)

Workup

  1. additionare added dropwise to this suspension in the course of 20 minutes
  2. filtrationthe batch is filtered
  3. washthe residue on the filter is rinsed with tetrahydrofuran
  4. customevaporated in vacuo
  5. customThe resulting syrup is purified by chromatography (mobile phase methylene chloride/methanol, 20:1)

Sources & evidence

ORD record
ord-c8145c9bcd494f00b53d6e76f7372890
Source dataset
uspto-grants-1987_10
Patent number
US04699899

Linked notes

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