N-Methyl-D-glucamine → N-(2-ethylhexyloxycarbonyl)-N-methyl-D-glucamine
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(=O)([O-])O.[Na+].Cl[C:20]([O:22][CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:21]>O.O1CCCC1.CC(C)=O>[CH2:29]([CH:24]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][O:22][C:20]([N:2]([CH3:1])[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])=[O:21])[CH3:30]Participants
Conditions
- Temperature
- 5 °C
Procedure
In a reactor, 117 g (0.6 mol) of N-methyl-D-glucamine were dissolved in a mixture of 800 ml of water and 400 ml of tetrahydrofuran, and 201.6 g (2.4 mol) of sodium hydrogen carbonate were then dispersed. While the temperature of the reaction mixture was maintained at 5° C., 115.6 g (0.6 mol) of 2-ethylhexyl chloroformate were added dropwise, and the mixture was then allowed to react for 3 hours with stirring at 5° C. and left standing overnight at room temperature. The reaction mixture was then filtered and concentrated; the pasty residue obtained was dissolved in 2 liters of acetone and then filtered after cooling to 5° C. The crystallized product collected was dried. 105 g (50% yield) of N-(2-ethylhexyloxycarbonyl)-N-methyl-D-glucamine, the melting point of which is 74° C., were obtained.
Workup
- additionwere then dispersed
- customto react for 3 hours
- waitleft
- filtrationThe reaction mixture was then filtered
- concentrationconcentrated
- customthe pasty residue obtained
- filtrationfiltered
- temperatureafter cooling to 5° C
- customThe crystallized product collected
- customwas dried
Sources & evidence
- ORD record
- ord-774e7cff87054fc098cc64b519894e8d
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05587169
Reaction notes
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