Hydrochloric Acid → HCID 16781337, compound
Reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].Cl.C(OCC)(=O)C>O1CCOCC1.[OH-].[Na+]>[CH2:1]([S:3]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:5])=[O:4])[CH3:2]Participants
Procedure
A solution of ethanesulfonyl chloride (3.9 ml, 41.1 mmol) in dioxane (10 ml) was added to a solution of 6-aminohexanoic acid (2 g, 15.2 mmol) in 1N NaOH (56 ml) and dioxane (10 ml), while stirring at 0° C.-5° C. The pH of the reaction mixture was adjusted to 8-9 by addition of 25% sodium hydroxide solution. The mixture was allowed to warm to room temperature and stirred for 30 minutes. Further 25% NaOH solution was added to adjust the pH to about 11. After 3.5 h 1N hydrochloric acid (15 ml) and ethyl acetate (60 ml) were added. The organic layer was dried over sodium sulfate and concentrated. The residue was triturated with a mixture of diethyl ether (5 ml) and hexane (15 ml). The solid was collected by filtration and dried affording 1.3 g of the title compound (40% yield).
Workup
- stirringstirred for 30 minutes
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated
- customThe residue was triturated with a mixture of diethyl ether (5 ml) and hexane (15 ml)
- filtrationThe solid was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-193d874a2858432682aa1b45e3d2dd4d
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576206B2
Reaction notes
Loading…