Cesium carbonate → HCID 67508812, compound

Temperature

50 °C

The crude benzyl 4-mercapto-2-methylbutan-2-ylcarbamate (2.83 g, 10.2 mmol) from the previous reaction was dissolved into dimethylformamide (60 mL). Cesium carbonate (6.65 g, 2 equiv, 20.4 mmol) was added in one portion to the solution to give a suspension followed by 2-(2-chloroethoxy)ethanol (1.39 g, 11.2 mmol). The flask was sealed with a septum and vigorously stirred at 50° C. under nitrogen atmosphere for 16 hours. The suspension was concentrated to an oily solid residue. This material was mixed with ethyl acetate (200 mL) and water (50 mL). The layers were separated and the organic layer was washed with brine (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a yellow oil. The crude oil was used without purification (2.23 g, 64.3%). LRMS (ESI/APCI) m/z 342 [M+H]+.

1. customto give a suspension
2. customThe flask was sealed with a septum
3. concentrationThe suspension was concentrated to an oily solid residue
4. additionThis material was mixed with ethyl acetate (200 mL) and water (50 mL)
5. customThe layers were separated
6. washthe organic layer was washed with brine (2×50 mL)
7. dry with materialThe organic layer was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated to a yellow oil
10. customThe crude oil was used without purification (2.23 g, 64.3%)

ORD record

ord-94f2d29ae3df4df497b6039a4bbc2a17

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09248117B2