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lithium hydroxide in tetrahydrofuran; methanol T=60°C; 9 h;

1: aq. NaOH / methanol / 6 h / 60 °C 2: 85 percent / DCC / dimethylformamide / 24 h View Scheme

1: trifluoroacetic acid / CH2Cl2; H2O / 0.5 h 2: 0.15 g / 3-(diethoxy-phosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / CH2Cl2 / 17 h 3: LiOH / tetrahydrofuran; methanol / 5 h / 60 °C View Scheme

1: trifluoroacetic acid / CH2Cl2; H2O / 0.5 h 2: 0.15 g / 3-(diethoxy-phosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; triethylamine / CH2Cl2 / 17 h View Scheme

trifluoroacetic acid in dichloromethane; water 0.5 h;

1: 93 percent / aq. NaOH / methanol / 18 h / Heating 2: 1.) aq. Cs2CO2 / 1) H2O, EtOH; 2) DMF, 40 deg C, overnight 3: TFA / CH2Cl2 / 1 h 4: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 5: 95 percent / H2 / Pd/C / ethanol / 12 h View Scheme

1: 93 percent / aq. NaOH / methanol / 18 h / Heating 2: 1.) aq. Cs2CO2 / 1) H2O, EtOH; 2) DMF, 40 deg C, overnight 3: TFA / CH2Cl2 / 1 h 4: 1.) dicyclohexylcarbodiimide, HOBt, 2.) TEA / 1) CH2Cl2, 1 h; 2) CH2Cl2, 2 h, 0 deg C, 20 deg C (15 h) 5: 95 percent / H2 / Pd/C / ethanol / 12 h 6: 59 percent / TFA, EDC / dimethylformamide / Ambient temperature 7: 77 percent / H2 / Pd/C / dimethylformamide / 6 h / Ambient temperature View Scheme