Multi-step reaction with 18 steps
1: 73 percent / diisopropylethylamine / CH2Cl2 / Ambient temperature
2: 1.) LDA / 1.) THF, -70deg C, 30 min, 2.) THF, -70 deg C, 30 min
3: conc. HCl / methanol / 0.25 h / 50 °C
4: 72 percent / Et3N, sulfur / dimethylformamide / 1 h / 50 °C
5: 247 g / CHCl3 / Ambient temperature
6: 290 g / pyridine, AcOH / toluene / 1.5 h / Heating
7: 199 g / NaOH / ethanol / 1.5 h / Ambient temperature
8: Et3N / toluene / Heating
9: 70 percent / Lawesson's reagent / 1,2-dimethoxy-ethane / 1.5 h / 80 °C
10: 37 percent / dioxane / 2 h / 130 °C
11: 58 percent / TFA / CHCl3 / 0 °C
12: pyridinium dichromate (PDC) / dimethylformamide / 15 h / Ambient temperature
13: CHCl3
14: 8N NaOH / methanol / Heating
15: pyridine / CH2Cl2 / 0 °C
16: 31 percent / CHCl3 / Ambient temperature
18: 100 percent / TFA / CHCl3 / 0.5 h / 0 °C
With
Lawessons reagent; pyridine; hydrogenchloride; sodium hydroxide; dipyridinium dichromate; sulfur; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide;
In
1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.40.762