Multi-step reaction with 6 steps
1: 90 percent / Et3N, HOBT, DCC / tetrahydrofuran; CHCl3
2: 97 percent / 1 N NaOH / methanol / 0 deg C, 1 h; RT, 6 h
3: 67 percent / Et3N, DCC / tetrahydrofuran; CHCl3 / 0 deg C, 1h; RT, overnight
4: 72 percent / 1 N NaOH / methanol / 0 deg C, 1h; RT, 5 h
5: 1.) OHNSu, DCC, 2.) 1-hydroxybenzotriazole, DCC / 1.) DMF, -20 deg C, 0.5 h; 0 deg C, 1 h, RT, overnight, 2.) DMF, 0 deg C
6: 95 percent / H2 / PdO / methanol / 3 h / Ambient temperature
With
sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide;
trimethyleneglycol;
In
tetrahydrofuran; methanol; chloroform;
DOI:10.1021/jm00118a005