Hydrochloric Acid → (4-Methanesulfonylamino-butoxy)-acetic Acid Ethyl Ester

Temperature

100 °C

To a mixture of NaH (60% in oil, 167 mg, 4.18 mmol) and DMF (10 mL) was added a solution of methanesulfonamide (398 mg, 4.18 mmol) in DMF (5 mL). The mixture was heated at 100° C. for 1.5 h and was cooled to room temperature. A solution of (4-bromo-butoxy)-acetic acid ethyl ester (1.000 g, 4.182 mmol) in DMF (10 mL) was added and the reaction was heated at 100° C. for 21 h. Water was added to the cooled reaction mixture and the aqueous solution was acidified to pH=2 with concentrated HCl. The aqueous solution was extracted with EtOAc (4×) and the organic solution was dried (MgSO4), filtered, and concentrated. The product was purified by flash chromatography (60% EtOAc/hexanes) to afford the title compound (181 mg). 1H NMR (400 MHz, CDCl3) δ4.90 (m, 1H), 4.20 (q, 2H), 4.04 (s, 2H), 3.54 (m, 2H), 3.16 (m, 2H), 2.93 (s, 2H), 1.69 (m, 4H), 1.26 (t, 3H); MS 254.1 (M+1).

1. temperaturewas cooled to room temperature
2. temperaturethe reaction was heated at 100° C. for 21 h
3. extractionThe aqueous solution was extracted with EtOAc (4×)
4. dry with materialthe organic solution was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe product was purified by flash chromatography (60% EtOAc/hexanes)

ORD record

ord-d1e2104fb7bc4d48ab55556db5826a9e

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06344485B1