Multi-step reaction with 4 steps
1: 1.) H2, TFA, 2.) HATU, collidine / 1.) 10 percent Pd/C / 1.) MeOH, 1 atm, 13 h, 2.) 0 deg C, 2 h; room temperature, 16 h
2: 1.) HOAt, DCC, 2.) TFA, 3.) collidine / 1.) DMF, CH2Cl2, 0 deg C, 2 h; room temperature, 7 h, 2.) 1.5 h, 3.) DMF, 0 deg C, 2 h; room temperature, 12 h
3: 1.) pentafluorophenol, DCC, 2.) TFA, 3.) phosphate buffer / 1.) EtOAc, 0 deg C, 1.5 h; room temperature, 6.5 h, 2.) 20 min, 3.) pH 9.5, 30 min
4: 44 percent / 1M LiOH / tetrahydrofuran; H2O / 0.67 h / 0 °C
With
2,3,5-trimethyl-pyridine; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; phosphate buffer; 2,3,4,5,6-pentafluorophenol; hydrogen; dicyclohexyl-carbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; water;
DOI:10.1016/S0968-0896(98)00254-5