Triethylamine → HCID 9967859, compound
Reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:11][C@H:12]([CH2:17][OH:18])[C@H:13]([CH2:15][CH3:16])[CH3:14].C(N(CC)CC)C.CCOC(C)=O.CCCCCC>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([S:7]([NH:11][C@H:12]([CH2:17][OH:18])[C@@H:13]([CH3:14])[CH2:15][CH3:16])(=[O:9])=[O:8])=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
5-Bromothiophene-2-sulfonyl chloride (5.0 g, 19.11 mmol) was added dropwise (5 min) as a solution in CH2Cl2 (10 mL) to a 0° C. solution of L-isoleucinol (2.108 g, 18.16 mmol) in CH2Cl2 (15 mL) and triethylamine (3.77 mL, 27.24 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 in methylene chloride (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 off-yellow solid (5.2 g). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluent: starting with 1:4 EtOAc-hexane and ending with 1:1 EtOAc-hexane to furnish 5-bromo-N-[(1S,2S)-1-(hydroxymethyl)-2-methylbutyl]-2-thiophenesulfonamide as an amorphous white solid (4.3 g, 70.49%). Mass Spectrum (−ESI): 246 (M−H)−.
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 off-yellow solid (5.2 g)
- customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluent
Sources & evidence
- ORD record
- ord-9a9591a1938649dbbe163d2928e097aa
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691884B2
Reaction notes
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