Multi-step reaction with 14 steps
1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane
2.1: acetic acid / methanol / 0.17 h
3.1: acetic acid; sodium cyanoborohydride / methanol / 2.5 h / Reflux
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4 h / 20 °C / Cooling
5.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1.5 h / 20 °C
7.1: triethylamine / dimethyl sulfoxide / 26 h / 100 °C
8.1: dmap / acetonitrile / 2 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h
10.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1.5 h / -78 °C
10.2: 1 h / -78 - -30 °C
11.1: cyclohexene; sodium chlorite; sodium dihydrogen phosphate monohydrate / tert-butyl alcohol; water / 2.5 h / Cooling with ice
12.1: palladium on carbon; hydrogen / methanol / 4 h
13.1: sodium carbonate / water; 1,4-dioxane / 0 - 20 °C
13.2: pH 3
14.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 22 h
14.2: 0.33 h
With
dmap; sodium chlorite; sodium dihydrogen phosphate monohydrate; oxalyl dichloride; palladium on carbon; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium cyanoborohydride; sodium carbonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; cyclohexene;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
1.1: |Swern Oxidation / 1.2: |Swern Oxidation / 10.1: |Swern Oxidation / 10.2: |Swern Oxidation;
DOI:10.1016/j.bmc.2013.01.020