Table 1.
A summary of the radiochemical and solvolytic properties of synthesized difluoro-dioxaborinin compounds.
| Compounds | RCY (%) by HPLC | RCY (%) by silica TLC (n = 3) | Isolated RCY | Stability (t1/2, h) 90% H2O/10% DMSO | Stability (t1/2, h) 10% H2O/90% DMSO | Fold increase in stability (90% to 10% H2O) |
|---|---|---|---|---|---|---|
| 1 | 99 | 69.6 ± 12.6 | 2.73 ± 0.02 | 7.63 ± 0.18 | 2.8 | |
| 2 | 97 | 67.0 ± 12.7 | 17.1 ± 0.7 | 53.9 ± 1.1 | 3.2 | |
| 3 | 97 | 69.9 ± 12.8 | 15.2 ± 0.5 | 53.9 ± 1.5 | 3.5 | |
| 5 | 93 | 64.1 ± 12.6 | 49.9 | - | 391 ± 4 | |
| 6 | 99 | 68.5 ± 12.7 | 5.19 ± 0.15 | 24.6 ± 0.5 | 4.7 | |
| 9 | 75 | 61.6 ± 12.6 | 37.3 | - | 11.9 ± 0.4 | |
| 10 | 80 | 64.4 ± 12.6 | - | 16.0 ± 0.2 | ||
| 13 | 98 | 68.0 ± 12.6 | - | 10.7 ± 1.8 | ||
| 14 | 98 | 67.5 ± 12.5 | - | 4.46 ± 0.05 | ||
| 15 | 98 | 66.0 ± 12.4 | 6.75 ± 0.19 | 33.7 ± 1.1 | 5.0 | |
| 16 | 88 | 67.2 ± 12.5 | - | 118 ± 12 | ||
| 17 | 92 | 73.8 ± 12.9 | - | 122 ± 3 |
Radiochemical and solvolytic measurements on the compounds shown in Figure 2. RCYs were determined after a 30 min, room-temperature radiolabeling. Solvolytic stability was determined by 19F NMR (Supporting Information Section 13). ‘–’ denote solvolytic stabilities that could not be determined due to compound insolubility.