Water → Methylsulfamic acid 2-hydroxy-3-(2-methoxyphenoxy)propyl ester
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([OH:14])[CH2:12][OH:13].N1C=CC=CC=1.[CH3:21][NH:22][S:23](Cl)(=[O:25])=[O:24].O>C(Cl)Cl>[OH:14][CH:11]([CH2:10][O:9][C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:12][O:13][S:23](=[O:25])(=[O:24])[NH:22][CH3:21]Participants
Procedure
A solution of 26.5 g (0.13 mole) of glycerol guaiacolate in 100 ml of methylene chloride and 10.8 ml (0.13 mole) of pyridine was added in a thin stream to a stirred solution of 17.1 g (0.13 mole) of N-methylsulfamoyl chloride (Preparation 22) in 70 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature for 2 hr. The reaction mixture was treated with 150 ml of water, the layers were separated, and the organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure to yield a viscous oil. The oil was purified by preparative high pressure liquid chromatography. Fractions containing the desired product were combined and the solvents evaporated under reduced pressure to give 13.9 g (37%) of the title compound as a yellow gum.
Workup
- customthe layers were separated
- washthe organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water
- dry with materialdried (magnesium sulfate)
- customthe solvent was evaporated under reduced pressure
- customto yield a viscous oil
- customThe oil was purified by preparative high pressure liquid chromatography
- additionFractions containing the desired product
- customthe solvents evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6cc78a9fc44b4c2abb3ab5adeb384dcb
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05192785
Reaction notes
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