N-Methyl-D-glucamine → N-methyl-N-[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]docosanamide
Reaction equation
[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].[C:14](Cl)(=[O:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].CO.C(Cl)(Cl)Cl>[OH-].[Na+].O1CCCC1>[CH3:1][N:2]([CH2:3][C@H:4]([OH:5])[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@H:10]([OH:11])[CH2:12][OH:13])[C:14](=[O:36])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]Participants
6
Procedure
N-Methyl glucamine (1.95 g, 10.0 mmol) was dissolved in 10 mL of 1.00 N sodium hydroxide solution and 10 mL of tetrahydrofuran. Docosanoyl chloride (3.58 g, 10.0 mmol) was then added to the rapidly stirred solution followed by another 20 mL portion of tetrahydrofuran. After stirring for 60 min, the thick reaction mixture was placed on a rotary evaporator and tetrahydrofuran was removed under reduced pressure. The resulting thick slurry was filtered, washed with water and dried with suction to give a waxy white solid. Chromatography (SiO2, 15%-30% MeOH/CHCl3) yielded 1.52 g of the following compound as a waxy solid.
Workup
- customthe thick reaction mixture was placed on a rotary evaporator and tetrahydrofuran
- customwas removed under reduced pressure
- filtrationThe resulting thick slurry was filtered
- washwashed with water
- customdried with suction
- customto give a waxy white solid
Sources & evidence
- ORD record
- ord-11fa651d44cf4445ad9527da40e0d4c6
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557893B2
Reaction notes
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