Thiophenol → 3-((tert-butyl(dimethyl)silyl)oxy)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-1-propanamine

N-(3-((tert-butyl(dimethyl)silyl)oxy)propyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.540 g, 1.01 mmol) and thiophenol (0.333 g, 3.02 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.557 g, 4.03 mmol) was added and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and filtered to remove unwanted solids. The crude filtrate was concentrated in vacuo, redissolved in methanol, and loaded onto a strong cation exchange resin cartridge to capture the desired product. Undesired materials were eluted from the cartridge with methanol, and then the desired material was released from the resin by elution with 2M ammonia in methanol. Concentration in vacuo gave the title compound as a yellow oil (0.294 g, 83% yield). No further purification was performed and the mixture was carried forward to the next step. LCMS: m/z 351 (M+H+), 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.06 (s, 6H) 0.90 (s, 9H) 1.75 (quin, J=6.46 Hz, 2H) 2.69-2.72 (m, 2H) 2.72-2.80 (m, 4H) 3.00-3.11 (m, 8H) 3.70 (t, J=6.02 Hz, 2H).

1. filtrationfiltered
2. customto remove unwanted solids
3. concentrationThe crude filtrate was concentrated in vacuo
4. dissolutionredissolved in methanol
5. washUndesired materials were eluted from the cartridge with methanol
6. washthe desired material was released from the resin by elution with 2M ammonia in methanol
7. concentrationConcentration in vacuo

ORDレコード

ord-88fdcf04cc75478c8f69c14513d441b0

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08846647B2