Multi-step reaction with 11 steps
1.1: DIPEA / acetonitrile / 20 - 60 °C
2.1: 101.5 g / DIPEA / acetonitrile / 24 h / 70 °C
3.1: 93.7 percent / TFA / CH2Cl2 / 70 h / 20 °C
4.1: TEA; DCC / CH2Cl2 / 20 h / 20 °C
5.1: hydroxylamine / ethanol; tetrahydrofuran / 3 h / 20 °C / pH 6.0
6.1: ethanol; H2O / Heating
7.1: 54 g / DIPEA / CH2Cl2 / 2 h / -40 °C
8.1: LHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -78 °C
8.2: 56 percent / 2 h
9.1: DIPEA; DMAP / CH2Cl2 / -23 - 20 °C
10.1: 26 percent / DDQ / CH2Cl2; H2O
With
dmap; TEA; hydroxylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo015665d