Multi-step reaction with 11 steps
1: H2 / PtO2 / methanol; dimethylformamide / 2 h / Ambient temperature
2: NEt3 / H2O; dioxane / 1) 0 deg C to RT, 30 min, 2) RT, overnight
3: 86 percent / NaH / tetrahydrofuran / 48 h / Ambient temperature
4: 96 percent / NEt3, hydroxybenzotriazole, dicyclohexylcarbodiimide / CH2Cl2; tetrahydrofuran / 1) 0 deg C, 2 h, 2) RT, overnight
5: 65 percent / HCl / ethyl acetate / 3.5 h / 0 °C
6: 92 percent / ethyl acetate / Ambient temperature
7: 89 percent / CH2Cl2 / Ambient temperature
8: 48 percent / Boc-L-alanine, NMM, HOBt, DCC / CH2Cl2; tetrahydrofuran / 1) 0 deg C, 2 h, 2) RT, overnight
9: 40 percent / HCl / ethyl acetate / 1) 0 deg C, 1.5 h, 2) RT, 1 h
10: 85 percent / N-methylmorpholine, hydroxybenzotriazole, dicyclohexylcarbodiimide / CH2Cl2; tetrahydrofuran / 1) 0 deg C, 2 h, 2) RT, overnight
11: 86 percent / 1) TFA, 2) NaHCO3 / 1) CH2Cl2, 0 deg C, 2) EtOAc
With
4-methyl-morpholine; hydrogenchloride; L-N-Boc-Ala; hydrogen; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;
platinum(IV) oxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;