Dichloromethane → HCID 67276511, compound

Temperature

0 °C

(2S)-2-Aminobutan-1-ol (2.1 mL, 22 mmol) and triethylamine (3.8 mL, 27 mmol) were dissolved in methylene chloride (30 mL, 500 mmol) and the solution was stirred at 0° C. for 5 minutes. Then, p-toluenesulfonyl chloride (4.3 g, 22 mmol) was added and the reaction mixture was stirred and permitted to warm to room temperature. The reaction was quenched with water and the phases were separated. The aqueous phase was extracted with 1×50 mL of DCM. The combined organic phases were washed with 1N HCl (50 mL), sat. NaHCO3 (50 mL) and brine (50 mL), dried with Magnesium sulfate, filtered and concentrated to give a white solid. The crude material was crystallized in ether/hexane to give (S)—N-(1-hydroxybutan-2-yl)-4-ethylbenzenesulfonamide as a white solid: 1H NMR (400 MHz, DMSO) δ 7.69 (d, J=8.2 Hz, 2H), 7.38 (t, J=9.0 Hz, 3H), 4.62 (t, J=5.6 Hz, 1H), 3.24 (dd, J=10.3, 5.2 Hz, 1H), 3.18-3.02 (m, 1H), 2.92 (dd, J=7.9, 4.2 Hz, 1H), 1.61-1.39 (m, 1H), 1.19 (dd, J=14.5, 7.1 Hz, 1H), 0.63 (t, J=7.4 Hz, 3H); LC-MS: m/z=244 (M+H).

1. stirringthe reaction mixture was stirred
2. temperatureto warm to room temperature
3. customThe reaction was quenched with water
4. customthe phases were separated
5. extractionThe aqueous phase was extracted with 1×50 mL of DCM
6. washThe combined organic phases were washed with 1N HCl (50 mL), sat. NaHCO3 (50 mL) and brine (50 mL)
7. dry with materialdried with Magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a white solid
11. customThe crude material was crystallized in ether/hexane

ORD record

ord-98e59b85da2243099e84da109ba48e3b

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163763B2