反应详情

To a solution of the title compound from Example 224 Step C (0.5 mmol, 191 mg) and DIEA (0.6 mmol, 104 μL) in 2 mL of DCM was added thiophosgene (0.5 mmol, 38 μL) (exothermic). After 15 min, the title compound from Example 14 Step B (0.6 mmol, 91 mg) was added to the reaction, followed by DIEA (0.6 mmol, 104 μL). The reaction mixture was allowed to stand at ambient temperature for 1 h, then Hg(O2CCF3)2 (0.6 mmol, 256 mg) was added (exothermic), affording a pinkish precipitate. After 30 min the solution was poured into saturated NaHCO3 containing Na2S, and the slurry was filtered through celite. The filter cake was washed with DCM. The organic layer of the filtrate and washings was collected and the aqueous phase was extracted with 2×DCM. The combined organic phase was dried with Na2SO4 and concentrated under reduced pressure affording a brown residue. Purification by flash chromatography on silica eluting with 20% EtOAc/hexanes afforded the product as a slightly green foam. MS (ESI): m/z 542 (M+H), 544. HPLC A: 2.67 min.

1. waitto stand at ambient temperature for 1 h
2. customaffording a pinkish precipitate
3. additioncontaining Na2S
4. filtrationthe slurry was filtered through celite
5. washThe filter cake was washed with DCM
6. customThe organic layer of the filtrate and washings was collected
7. extractionthe aqueous phase was extracted with 2×DCM
8. dry with materialThe combined organic phase was dried with Na2SO4
9. concentrationconcentrated under reduced pressure
10. customaffording a brown residue
11. customPurification by flash chromatography on silica eluting with 20% EtOAc/hexanes
12. customafforded the product as a slightly green foam
13. custom2.67 min.