acetic acid in 1,4-dioxane T=40°C; 12 h;

Amberlite IR 45 (acetate form); hydrogen; palladium on activated charcoal; Rh on carbon in acetic acid 6 h;

1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide in various solvent(s) 16 h; Ambient temperature;

trifluorormethanesulfonic acid; methyl-phenyl-thioether; 3-methyl-phenol; trifluoroacetic acid 1 h; Ambient temperature;

1: 70 percent / 1-hydroxybenzotriazole, DCC, Et3N / dimethylformamide / 0 deg C to room temperature 2: TFA / 0.5 h / Ambient temperature 3: 79 percent / Et3N / dimethylformamide / 16 h 4: 76 percent / Amberlite IR 45 (acetate form), H2 / Rh-C, Pd-C / aq. acetic acid / 6 h View Scheme

1: 73 percent / NaOH / methanol / 1 h 2: 70 percent / 1-hydroxybenzotriazole, DCC, Et3N / dimethylformamide / 0 deg C to room temperature 3: TFA / 0.5 h / Ambient temperature 4: 79 percent / Et3N / dimethylformamide / 16 h 5: 76 percent / Amberlite IR 45 (acetate form), H2 / Rh-C, Pd-C / aq. acetic acid / 6 h View Scheme

1: TFA / 0.5 h / Ambient temperature 2: 79 percent / Et3N / dimethylformamide / 16 h 3: 76 percent / Amberlite IR 45 (acetate form), H2 / Rh-C, Pd-C / aq. acetic acid / 6 h View Scheme

1: 25 percent / Et3N, Br2 / CHCl3 / 0 deg C to room temperature 2: 73 percent / NaOH / methanol / 1 h 3: 70 percent / 1-hydroxybenzotriazole, DCC, Et3N / dimethylformamide / 0 deg C to room temperature 4: TFA / 0.5 h / Ambient temperature 5: 79 percent / Et3N / dimethylformamide / 16 h 6: 76 percent / Amberlite IR 45 (acetate form), H2 / Rh-C, Pd-C / aq. acetic acid / 6 h View Scheme

1: 78.9 percent / BOP, HOBt, N-methylmorpholine / dimethylformamide / 4 °C 2: 80.3 percent / 1M TFMSA-thioanisole/TFA, m-cresole / 1 h / Ambient temperature View Scheme

2: 60 percent / N-hydroxysuccinimide, dicyclohexylcarbodiimide / various solvent(s) / 16 h / Ambient temperature View Scheme