Multi-step reaction with 14 steps
1: 0.135 g / 2,4,6-trimethylpyridine; 7-aza-1-hydroxybenzotriazole / ethyl acetate / 15 h / 20 °C
2: aq. HCl / ethyl acetate / 3 h / 20 °C
3: 0.122 g / 2,4,6-trimethylpyridine; i-Pr2NEt / acetonitrile / 16 h / 20 °C
4: Et2NH / acetonitrile / 0.67 h / 20 °C
5: 0.104 mg / N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride; 7-aza-1-hydroxybenzotriazole; 2,4,6-trimethylpyridine / CH2Cl2 / 16 h / 20 °C
6: 73 percent / aq. tetra-n-butylammonium hydroxide / tetrahydrofuran / 0.75 h / 0 °C
7: 93 percent / O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium*PF6; 7-aza-1-hydroxybenzotriazole; 2,4,6-trimethylpyridine / i-Pr2NEt / CH2Cl2 / 15 h / 20 °C
8: 98 percent / Bu4N(+)F(-) / acetonitrile / 2 h / 20 - 55 °C
9: aq. HCl / ethyl acetate / 1 h / 20 °C
10: 31.6 mg / O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium*PF6; 7-aza-1-hydroxybenzotriazole; i-Pr2NEt / CH2Cl2 / 22 h / 20 °C
11: anisole; TFA / 2 h / 20 °C
12: 32.5 mg / O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium*PF6; 7-aza-1-hydroxybenzotriazole; 2,4,6-trimethylpyridine / i-Pr2NEt / CH2Cl2 / 15 h / 20 °C
13: TFA / 1 h / 20 °C
14: 25.0 mg / O-(7-azabenzotriazole-1-yl)-N,N,N',N'-tetramethyluronium*PF6; 7-aza-1-hydroxybenzotriazole; 2,4,6-trimethylpyridine / i-Pr2NEt / CH2Cl2 / 4 h / 20 °C
With
2,4,6-trimethyl-pyridine; hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; methoxybenzene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid;
N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1002/chem.200400977