Ethanesulfonyl chloride → 8-(Ethylsulfonylamino)octanoic acid

A solution of ethanesulfonyl chloride (1.5 ml, 15.7 mmol) in dioxane (5 ml) was added to a solution of 8-aminooctanoic acid (1 g, 6.28 mmol) in 1N NaOH (22 ml) and dioxane (5 ml), while stirring at 0° C.-5° C. The mixture was allowed to warm to room temperature and stirred for 3.5 minutes. During this period, at 1 hour intervals, the pH was adjusted to 7-8 by addition of 25% NaOH solution. The reaction mixture was washed with diethyl ether (30 ml). The pH was adjusted to 1-2 by addition of 1N HCl and the mixture was extracted with ethyl acetate (70 ml). The organic layer was dried over sodium sulfate and concentrated. The residue was triturated with a mixture of diethyl ether. The solid was collected by filtration and dried under vacuum affording 600 mg of the title compound (38% yield).

1. stirringstirred for 3.5 minutes
2. waitDuring this period
3. washThe reaction mixture was washed with diethyl ether (30 ml)
4. additionThe pH was adjusted to 1-2 by addition of 1N HCl
5. extractionthe mixture was extracted with ethyl acetate (70 ml)
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was triturated with a mixture of diethyl ether
9. filtrationThe solid was collected by filtration
10. customdried under vacuum

ORD record

ord-86e7507dbec247bd9c4c26f229db5248

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233115B2