Triethylamine → HCID 59086186, compound
Reaction equation
[Cl: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]([CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)[CH2:13][OH:14].C(N(CC)CC)C.CCOC(C)=O.CCCCCC>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:11][C@@H:12]([CH:15]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16]2)[CH2:13][OH:14])(=[O:9])=[O:8])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 25 °C
Procedure
5-Chlorothiophene-2-sulfonyl chloride (0.856 g, 3.94 mmol) was added dropwise (5 min) as a solution in CH2Cl2 (5 mL) to a 0° C. solution of (2S)-2-amino-2-(2,3-dihydro-1H-inden-2-yl)ethanol (0.46 g, 2.63 mmol) in CH2Cl2 (5 mL) and triethylamine (3.8 mL, 5.26 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 (50 mL) and the organic layer was washed with 1N HCl (2×50 mL), saturated aqueous NaCl (50 mL). The organic layer was dried over MgSO4, filtered and concentrated to obtain a crude oil (0.89 g). The crude product was purified by column chromatography, silica gel 230-400 mesh, eluant: 1:4 EtOAc-hexane to afford 5-chloro-N-[(1S)-1-(2,3-dihydro-1H-inden-2-yl)-2-hydroxy ethyl]thiophene-2-sulfonamide as an amorphous white solid (0.361 g, 38.4%). Mass Spectrum (−ESI): 356 (M−H)−. Anal. Calc'd for C15H10ClNO3S2: C, 50.34; H, 4.51 N, 3.91 Found: C, 50.28; H, 4.36 N, 3.77.
Workup
- washthe organic layer was washed with 1N HCl (2×50 mL), saturated aqueous NaCl (50 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto obtain a crude oil (0.89 g)
- customThe crude product was purified by column chromatography, silica gel 230-400 mesh, eluant
Sources & evidence
- ORD record
- ord-7e8354357bc24e0a875b3223f0db66c6
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842718B2
Reaction notes
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