Multi-step reaction with 13 steps
1.1: 70 percent / H2 / Pd(OH)2 / methanol
2.1: 96 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotrazole; diisopropylethylamine
3.1: LiOH / methanol; H2O
4.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotrazole; diisopropylethylamine
5.1: trifluoroacetic acid
6.1: Bu4NF; TsOH
6.2: pentafluorophenol; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride
6.3: NaHCO3 / dimethylformamide / 45 °C
7.1: trifluoroacetic acid
8.1: 80 percent / NaHCO3 / acetonitrile
9.1: Bu4NF / tetrahydrofuran
10.1: trimethylphosphine / tetrahydrofuran
11.1: diphenylphosphoryl azide / dimethylformamide / 336 h
12.1: LiOH / methanol; tetrahydrofuran
13.1: Amberlyst-15 / methanol; H2O
With
lithium hydroxide; amberlyst-15; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trimethylphosphane;
palladium dihydroxide;
In
tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.200352423