Reaction conditions investigation of the Sn2/lactamization process.
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Entry | Base (1 eq.) | M | T (°C) | t | Yielda/notes |
1 | — | 0.20 | rt | 96 h | Sm in complex mixture |
2 | — | 0.20 | 50 | 24 h | 30% |
3 | NaHCO3 | 0.20 | 50 | 48 h | No react. |
4 | K2CO3 | 0.20 | 50 | 24 h | 45% |
5 | DIPEA | 0.20 | 50 | 24 h | 80% |
6 | DIPEA | 0.10 | 50 | 24 h | 57% |
7 | DIPEA | 0.20 | rt | 24 h | Sm and acyclic intermediate |
8 | DIPEA | Solvent free | rt | 24 h | Sm and acyclic intermediate |
9 | DIPEA | Solvent free | 50 | 24 h | Complex mixture of products |
Isolated yields by chromatography.