1: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h 2: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 3: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 4: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 5: sodium dithionite / dimethylformamide; H2O / 0.5 h 6: 0.1N NaOH / 1.5 h 7: Me2SO / dimethylformamide / 47 h 8: 0.1N NaOH / acetonitrile View Scheme

1: 82 percent / p-toluenesulfonic acid monohydrate / benzene / 6 h / Heating 2: 93.5 percent / 0.5 N NaOH / acetonitrile / 18 h / Ambient temperature 3: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h 4: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 5: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 6: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 7: sodium dithionite / dimethylformamide; H2O / 0.5 h 8: 0.1N NaOH / 1.5 h 9: Me2SO / dimethylformamide / 47 h 10: 0.1N NaOH / acetonitrile View Scheme

1: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h 2: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 3: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 4: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 5: sodium dithionite / dimethylformamide; H2O / 0.5 h 6: 0.1N NaOH / 1.5 h 7: Me2SO / dimethylformamide / 47 h 8: 0.1N NaOH / acetonitrile View Scheme

1: 93.5 percent / 0.5 N NaOH / acetonitrile / 18 h / Ambient temperature 2: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h 3: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 4: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 5: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 6: sodium dithionite / dimethylformamide; H2O / 0.5 h 7: 0.1N NaOH / 1.5 h 8: Me2SO / dimethylformamide / 47 h 9: 0.1N NaOH / acetonitrile View Scheme

1: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 2: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 3: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 4: sodium dithionite / dimethylformamide; H2O / 0.5 h 5: 0.1N NaOH / 1.5 h 6: Me2SO / dimethylformamide / 47 h 7: 0.1N NaOH / acetonitrile View Scheme

1: 82 percent / sodium azide, potassium iodide / acetone / 2 h 2: 82 percent / p-toluenesulfonic acid monohydrate / benzene / 6 h / Heating 3: 93.5 percent / 0.5 N NaOH / acetonitrile / 18 h / Ambient temperature 4: N-methylmorpholine, isobutyl chloroformate / 1.) DMF, 20 min, 2.) DMF, RT, 18 h 5: H2 / 5percent Pd/C / methanol / 18 h / 1292.9 Torr 6: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 7: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 8: sodium dithionite / dimethylformamide; H2O / 0.5 h 9: 0.1N NaOH / 1.5 h 10: Me2SO / dimethylformamide / 47 h 11: 0.1N NaOH / acetonitrile View Scheme

1: 2.) N-methylmorpholine / 1.) methanol, reflux, 1 h, 2.) methanol, 2 h 2: 94.8 percent / 1N HCl, trifluoroacetic acid / 55 °C 3: sodium dithionite / dimethylformamide; H2O / 0.5 h 4: 0.1N NaOH / 1.5 h 5: Me2SO / dimethylformamide / 47 h 6: 0.1N NaOH / acetonitrile View Scheme

1: sodium dithionite / dimethylformamide; H2O / 0.5 h 2: 0.1N NaOH / 1.5 h 3: Me2SO / dimethylformamide / 47 h 4: 0.1N NaOH / acetonitrile View Scheme