Triethylamine → HCID 59086199, compound

Temperature

25 °C

2-Furansulfonyl chloride (1.01 g, 8.69 mmol) was added dropwise (5 min) as a solution in CH2Cl2 (5 mL) to a 0° C. solution of L-isoleucinol (0.909 g, 7.83 mmol) in CH2Cl2 (20 mL) and triethylamine (2.42 mL, 17.38 mmol). The solution was allowed to warm to 25° C. overnight (19 h). An aliquot was taken and TLC (1:1 EtOAc-hexane) indicated that reaction was complete. It was diluted with CH2Cl2 (100 mL) and the organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated to obtain a crude black oil (0.65 g). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluent: starting with 1:3 EtOAc-hexane and ending with 1:2 EtOAc-hexane to furnish N-[(1S,2S)-1-(hydroxymethyl)-2-methylbutyl]-2-furansulfonamide as an amorphous white solid (0.155 g, 72.12%). Mass Spectrum (−ESI): 246 (M−H)−. Anal. Calc'd for C10H17ClNO4S: C, 48.57; H, 6.93; N, 5.66. Found: C, 48.72; H, 6.78; N, 5.39.

1. washthe organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customto obtain a crude black oil (0.65 g)
6. customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluent

ORD record

ord-09056e9eab9e456da9a8bf8d35eecc1a

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878742B2