Triethylamine → HCID 59086199, compound
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].C([N:12](CC)CC)C.CCO[C:20]([CH3:22])=[O:21].[CH3:23][CH2:24][CH2:25][CH2:26]CC>C(Cl)Cl>[OH:21][CH2:20][C@@H:22]([NH:12][S:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])=[O:7])[C@@H:25]([CH3:26])[CH2:24][CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
2-Furansulfonyl chloride (1.01 g, 8.69 mmol) was added dropwise (5 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.
Workup
- washthe organic layer was washed with 1N HCl (2×50 mL) and saturated aqueous NaCl (50 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto obtain a crude black oil (0.65 g)
- customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluent
Sources & evidence
- ORD record
- ord-966fa2aa8de2418eaad457159b299cb9
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610734B2
Reaction notes
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