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 0–5° 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). 1H NMR (DMSO-d6): 11.9 (1H, s); 6.96 (1H, t, J=6 Hz); 2.96 (2H, q, J=7.1); 2.88 (2H, q, J=6.6); 2.2 (2H, t, J=7.3); 1.45 (4H, m); 1.26 (6H, m); 1.18 (3H, t, J=7.3).

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-Eintrag

ord-872bfeb0b0ba49698f5da157e4508b9c

Quelldatensatz

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07223745B2