Multi-step reaction with 9 steps
1: TEMPO; NaOCl; KBr / acetone; H2O
2: 100 percent / H2 / Pd/C / ethanol / 760.05 Torr
3: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C
4: TFA; DMS / CH2Cl2 / 0 °C
5: 2,6-lutidine / CH2Cl2 / 0 °C
6: 80 percent / Cu(OAc)2; pyridine; O2 / CH2Cl2 / 20 °C
7: 99 percent / LiOH / methanol; H2O / 0 °C
8: TFA; DMS / CH2Cl2 / 0 °C
9: HATU; HOAt / CH2Cl2; dimethylformamide / 0 - 20 °C
With
pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 2,3-dimercapto-succinic acid; hydrogen; oxygen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja011943e