Multi-step reaction with 6 steps
1: 25.4 percent / NH2OH*HCl/NaOEt / ethanol / Heating
2: benzene / 0.5 h / Heating
3: hydrogen / 10 percent Pd/charcoal / methanol / 5 h / Ambient temperature
4: 100 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl3 / 1.) 0 deg C, 1 h, 2.) r.t., overnight
5: 87 percent / 1 M NaOH / ethanol; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 5 h
6: 61.6 percent / triethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl3 / 1.) 0 deg C, 1 h, 2.) r.t., overnight
With
sodium hydroxide; hydroxylamine hydrochloride; hydrogen; sodium ethanolate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; chloroform; water; benzene;
DOI:10.1021/jm00127a017