Multi-step reaction with 5 steps
1: 98 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl3 / 1.) 0 deg C, 1 h, 2.) r.t., overnight
2: 92.4 percent / 1 M NaOH / ethanol; H2O / 1.) 0 deg C, 1 h, 2.) r.t., 5 h
3: 22.4 percent / triethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl3 / 1.) 0 deg C, 1 h, 2.) r.t., overnight
4: 43.4 percent / trifluoroacetic acid / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) 4 deg C, overnight
5: 53.6 percent / hydrogen / 10 percent Pd/charcoal / methanol / 5 h / Ambient temperature
With
sodium hydroxide; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water;
DOI:10.1021/jm00127a017