trifluoroacetic acid in dichloromethane 0.116667 h;

1: 1.) 1-hydroxybenzotriazole hydrate, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, MeOH, overnight 2: 89 percent / TFA / CH2Cl2 / 1 h 3: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 4: 87 percent / TFA / CH2Cl2 / 0.17 h 5: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 6: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: Et3N / tetrahydrofuran / 0.67 h / 0 °C 2: LiBH4 / tetrahydrofuran / 6 h / 0 - 20 °C 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT 4: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min 5: aq. LiOH / dioxane / 16 h / Ambient temperature 6: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 7: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 2: 87 percent / TFA / CH2Cl2 / 0.17 h 3: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 4: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min 2: aq. LiOH / dioxane / 16 h / Ambient temperature 3: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 4: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT 2: 1.) t-BuOK / 1.) THF, RT, 40 min, 2.) THF, RT, 75 min 3: aq. LiOH / dioxane / 16 h / Ambient temperature 4: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 5: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 2: 87 percent / TFA / CH2Cl2 / 0.17 h 3: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 4: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 2: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: aq. LiOH / dioxane / 16 h / Ambient temperature 2: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 3: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme

1: 89 percent / TFA / CH2Cl2 / 1 h 2: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 3: 87 percent / TFA / CH2Cl2 / 0.17 h 4: 1.) 1-hydroxy-7-azabenzotriazole, 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride, 2.) diisopropylethylamine / 1.) CH2Cl2, DMF, 15 min, 2.) CH2Cl2, DMF, overnight 5: 41 percent / TFA / CH2Cl2 / 0.12 h View Scheme