Multi-step reaction with 10 steps
1: Zn, I2 / tetrahydrofuran / 0.5 h / Heating
2: 79 percent / NaOH / tetrahydrofuran / 4 h
3: 56 percent / HOBT, DCC / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 16 h
4: 93 percent / HCl gas / CHCl3; methanol / 1 h / Ambient temperature
5: 80 percent / HOBT, DCC / CH2Cl2 / 1.) 0 deg C, 2 h, 2.) RT, 16 h
6: 3.50 g / HCl gas / CH2Cl2; methanol / 0.25 h / Ambient temperature
7: HOBT, DCC, Et3N / dimethylformamide / 1.) 0 deg C, 1 h, 2.) RT, 16 h
8: HCl / CHCl3
9: 59 percent / formic acid / ethanol / 3 h / Heating
10: dichloroacetic acid, DCC, DMSO / CH2Cl2 / 1.) 0 deg C, 2.) RT, 18 h
With
hydrogenchloride; dichloro-acetic acid; sodium hydroxide; formic acid; iodine; benzotriazol-1-ol; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; zinc;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm00079a001