| 90% |
With potassium carbonate; In acetone; at 60℃; for 6h;Molecular sieve; |
Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, Ieq) were added to a solution of phenol 64 (400 mg, 0.84 mmol) in acetone (4 mL, dried overmolecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 15in 90% yield. LC/MS, 3.90 mm (ES+) m/z (relative intensity)670.91 ([M], 100). 1H NMR (400MHz, CDCI3) 5 7.23 (s, I H), 6.69 (s, I H), 6.60 (s, I H), 5.87 (d, J = 8.8 Hz, I H), 5.83 - 5.68(m, J = 5.6 Hz, I H), 5.15 - 5.01 (m, 2H), 4.67 -4.58 (m, I H), 4.45 - 4.35 (m, I H), 4.04 - 3.93(m, 2H), 3.91 (s, 3H), 3.73 (td, J= 10.0, 3.8 Hz, IH), 3.25-3.14 (m, J= 8.5, 7.0 Hz,2H), 2.92 (dd, J= 16.8, 10.3 Hz, IH), 2.38 (d, J= 16.8 Hz, IH), 1.95-1.81 (m, 4H), 1.77 (s,3H), 1.64-1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H). |
| 90% |
With potassium carbonate; In acetone; at 60℃; for 6h;Molecular sieve; |
Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, Ieq) were added to a solution of phenol 64 (400 mg, 0.84 mmol) in acetone (4 mL, dried overmolecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 15in 90% yield. LC/MS, 3.90 mm (ES+) m/z (relative intensity)670.91 ([M], 100). 1H NMR (400MHz, CDCI3) 5 7.23 (s, I H), 6.69 (s, I H), 6.60 (s, I H), 5.87 (d, J = 8.8 Hz, I H), 5.83 - 5.68(m, J = 5.6 Hz, I H), 5.15 - 5.01 (m, 2H), 4.67 -4.58 (m, I H), 4.45 - 4.35 (m, I H), 4.04 - 3.93(m, 2H), 3.91 (s, 3H), 3.73 (td, J= 10.0, 3.8 Hz, IH), 3.25-3.14 (m, J= 8.5, 7.0 Hz,2H), 2.92 (dd, J= 16.8, 10.3 Hz, IH), 2.38 (d, J= 16.8 Hz, IH), 1.95-1.81 (m, 4H), 1.77 (s,3H), 1.64-1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H). |
| 90% |
With potassium carbonate; In acetone; at 60℃; for 6h;Molecular sieve; |
Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (1 16 mg, 0.84 mmol, 1 eq) were added to a solution of phenol 14 (400 mg, 0.84 mmol) in acetone (4 mL, dried over molecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 15 in 90% yield. LC/MS, 3.90 min (ES+) m/z (relative intensity) 670.91 ([M]+, 100). 1H NMR (400 MHz, CDCIs) delta 7.23 (s, 1 H), 6.69 (s, 1 H), 6.60 (s, 1 H), 5.87 (d, J = 8.8 Hz, 1 H), 5.83 - 5.68 (m, J = 5.6 Hz, 1 H), 5.15 - 5.01 (m, 2H), 4.67 - 4.58 (m, 1 H), 4.45 - 4.35 (m, 1 H), 4.04 - 3.93 (m, 2H), 3.91 (s, 3H), 3.73 (td, J = 10.0, 3.8 Hz, 1 H), 3.25 - 3.14 (m, J = 8.5, 7.0 Hz, 2H), 2.92 (dd, J = 16.8, 10.3 Hz, 1 H), 2.38 (d, J = 16.8 Hz, 1 H), 1 .95 - 1 .81 (m, 4H), 1 .77 (s, 3H), 1.64 - 1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H). |
| 90% |
With potassium carbonate; In acetone; at 60℃; for 6h;Molecular sieve; |
Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, Ieq) were added to a solution of phenol 64 (400 mg, 0.84 mmol) in acetone (4 mL, dried overmolecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 15in 90% yield. LC/MS, 3.90 mm (ES+) m/z (relative intensity)670.91 ([M], 100). 1H NMR (400MHz, CDCI3) 5 7.23 (s, I H), 6.69 (s, I H), 6.60 (s, I H), 5.87 (d, J = 8.8 Hz, I H), 5.83 - 5.68(m, J = 5.6 Hz, I H), 5.15 - 5.01 (m, 2H), 4.67 -4.58 (m, I H), 4.45 - 4.35 (m, I H), 4.04 - 3.93(m, 2H), 3.91 (s, 3H), 3.73 (td, J= 10.0, 3.8 Hz, IH), 3.25-3.14 (m, J= 8.5, 7.0 Hz,2H), 2.92 (dd, J= 16.8, 10.3 Hz, IH), 2.38 (d, J= 16.8 Hz, IH), 1.95-1.81 (m, 4H), 1.77 (s,3H), 1.64-1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H). |
| 90% |
With potassium carbonate; In acetone; at 60℃; for 6h; |
Diiodopentane (0.63 niL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, 1 eq) were added to a solution of phenol 54 (400 mg, 0.84 mmol) in acetone (4 mL, dried over molecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 55 in 90% yield. LC/MS, 3.90 min (ES+) m/z (relative intensity) 670.91 ([M]+, 100). 1H NMR (400 MHz, CDC13) delta 7.23 (s, 1H), 6.69 (s, 1H), 6.60 (s, 1H), 5.87 (d, / = 8.8 Hz, 1H), 5.83 - 5.68 (m, J = 5.6 Hz, 1H), 5.15 - 5.01 (m, 2H), 4.67 - 4.58 (m, 1H), 4.45 - 4.35 (m, 1H), 4.04 - 3.93 (m, 2H), 3.91 (s, 3H), 3.73 (td, / = 10.0, 3.8 Hz, 1H), 3.25 - 3.14 (m, / = 8.5, 7.0 Hz, 2H), 2.92 (dd, J = 16.8, 10.3 Hz, 1H), 2.38 (d, / = 16.8 Hz, 1H), 1.95 - 1.81 (m, 4H), 1.77 (s, 3H), 1.64 - 1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H). |
| 90% |
With potassium carbonate; In acetone; at 60℃; for 6h;Molecular sieve; |
(f) (11 S, 1 la S)-aIIyI 1 1-((tert-butyldimethylsllyl) oxy)-8-((5-iodopentyl) oxy) - 7-methoxy-2- met hyl-5-oxo- 11, 1 la-dihydro- 1H-benzo[e]pyrrolo[1, 2-a][1, 4]diazepine- 1O(5H) -carboxyl ate(55)Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, 1 eq) were added to a solution of phenol 54 (400 mg, 0.84 mmol) in acetone (4 mL, dried over molecular sieves). The reaction mixture was then warmed to 6000 and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 55 in 90% yield. LC/MS, 3.90 mm (ES+) m/z (relative intensity) 670.91 ([M], 100). 1H NMR (400 MHz, ODd3) O 7.23 (5, 1H), 6.69 (5, 1H), 6.60 (5, 1H), 5.87 (d, J= 8.8 Hz, 1H), 5.83-5.68 (m, J= 5.6 Hz, 1H), 5.15-5.01 (m, 2H), 4.67-4.58 (m, 1H), 4.45-4.35(m, 1H), 4.04- 3.93 (m, 2H), 3.91 (5, 3H), 3.73 (td, J= 10.0, 3.8 Hz, 1H), 3.25-3.14 (m, J= 8.5, 7.0 Hz, 2H), 2.92 (dd, J= 16.8, 10.3 Hz, 1H), 2.38 (d, J= 16.8 Hz, 1H), 1.95-1.81 (m, 4H), 1.77 (5, 3H), 1.64-1.49 (m, 2H), 0.88 (5, 9H), 0.25 (5, 3H), 0.23 (5, 3H). |
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