Dodecanoyl chloride → N-Glucopyranosyl-N-octadecyldodecanamide

HRID 482670Notes

Reaction equation

HRID 482670 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(=O)([O-])[O-].[Na+].[Na+].[C:37](Cl)(=[O:49])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].C1(C)C=CC=CC=1.C(O)(C)C>O1CCCC1>[CH:20]1([N:19]([CH2:1][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:37](=[O:49])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[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]

Participants

6

Reactant 4

HCID 8166Dodecanoyl chlorideHCID 10340Sodium CarbonateHCID 13361749N-octadecylglucopyranosylamineHCID 21881414Toluene isopropyl alcohol

Product 1

HCID 13230937N-Glucopyranosyl-N-octadecyldodecanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 g of the compound from Example 1 are suspended in 20 ml of tetrahydrofuran, 10 g of sodium carbonate are added and 10 g of dodecanoyl chloride in 10 ml of tetrahydrofuran are then added dropwise. When the reaction is complete (checked by thin layer chromatography on silica gel 60 6:1 toluene/isopropanol), the solid is filtered off, the filtrate is evaporated in vacuo to a syrup, and the crude product is purified by column chromatography on silica gel 60 using 10:1 toluene/isopropanol as the mobile phase.

Workup

  1. filtrationthe solid is filtered off
  2. customthe filtrate is evaporated in vacuo to a syrup
  3. customthe crude product is purified by column chromatography on silica gel 60 using 10:1 toluene/isopropanol as the mobile phase

Sources & evidence

ORD record
ord-3563ef59a36b44ba9e0cb0b1afeebd0a
Source dataset
uspto-grants-1986_03
Patent number
US04574122

Reaction notes

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