反应详情

温度

60 °C

The Boc pyrrole trimer (5) (0.6 g, 1.2 mmol) was dissolved in MeOH (5 mL) and treated with NaOH solution (0.1 g in 5 mL H2O). The reaction mixture was stirred overnight then heated at 60° C. for 2 hours. The MeOH was removed in vacuo and the aqueous fraction extracted with EtOAc (25 mL). The aqueous layer was adjusted to pH 2-3 with 1M HCl solution then extracted with EtOAc (3×30 mL). The combined organic layers were dried over MgSO4 then concentrated in vacuo to give an orange solid. The solid was suspended in Et2O (10 mL) and collected on a filter then dried in vacuo to give an orange solid 0.431 g (74%). 1H NMR d6-DMSO δ 12.11 (1H, s, OH), 9.89 (1H, s, N—H), 9.86 (1H, s, N—H), 9.09 (1H, s, Boc-N—H), 7.43 (1H, d, J=1.9 Hz, Py-H), 7.22 (1H, d, J=1.7 Hz, Py-H), 7.06 (1H, d, J=1.7 Hz, Py-H), 6.90 (1H, s, Py-H), 6.86 (1H, d, J=1.9 Hz, Py-H), 6.84 (1H, s, Py-H), 3.85 (3H, s, N—CH3), 3.83 (3H, s, N—CH3), 3.82 (3H, s, N—CH3), 1.46 (9H, s, Boc-H); 13C NMR d6-DMSO δ 161.9, 158.4, 158.4, 152.8, 122.8, 122.7, 122.5, 122.4, 122.3, 120.2 (CH), 119.5, 118.4 (CH), 117.0 (CH), 108.4 (CH), 104.7 (CH), 103.8 (CH), 78.2, 36.1 (CH3), 36.0 (CH3), 28.1 ([CH3]3).

1. customThe MeOH was removed in vacuo
2. extractionthe aqueous fraction extracted with EtOAc (25 mL)
3. extractionthen extracted with EtOAc (3×30 mL)
4. dry with materialThe combined organic layers were dried over MgSO4
5. concentrationthen concentrated in vacuo
6. customto give an orange solid
7. customcollected on
8. filtrationa filter
9. customthen dried in vacuo