4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane T=25°C; Condensation; 0.5 h; Further stages.;

1: 3-hydroxyquinaldic acid With 4-(N,N-dimethlyamino)pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane T=25°C; 0.5 h; 2: (1R,7S,11S,14R,20S,24S)-7,20-Diamino-2,12,15,25-tetramethyl-11,24-bis-methylsulfanylmethyl-9,22,28,29-tetrathia-2,5,12,15,18,25-hexaaza-bicyclo[12.12.4]triacontan-3,6,10,13,16,19,23,26-octaone in dichloromethane T=25°C; 72 h; Further stages.;

1.1: H2O / 12 h / 25 °C / pH 8 2.1: 91 percent / benzene; methanol / 0 °C 3.1: 91 percent / HCl / ethyl acetate / 0.5 h / 25 °C 4.1: HOAt; EDCI / CH2Cl2 / 0.25 h / 0 °C 4.2: 78 percent / CH2Cl2 / 12 h 5.1: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C 6.1: 68 percent / HOAt; EDCI; NaHCO3 / CH2Cl2 / 12 h / 0 °C 7.1: 100 percent / aq. LiOH / tetrahydrofuran; methanol / 1.5 h / 25 °C 8.1: HOAt; EDCI / CH2Cl2 / 15 h / -20 °C 8.2: 49 percent / CH2Cl2 / 4 h 9.1: 100 percent / Zn; 90percent aq. AcOH / 2 h / 0 °C 10.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 11.1: Zn; 90percent aq. AcOH / 2 h / 0 °C 12.1: I2 / CH2Cl2; methanol / 2 h / 25 °C 13.1: 3 M HCl / dioxane / 0.5 h / 25 °C 14.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 15.1: TFA; anisole / 6 h / 25 °C 16.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 16.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: 91 percent / benzene; methanol / 0 °C 2.1: 91 percent / HCl / ethyl acetate / 0.5 h / 25 °C 3.1: HOAt; EDCI / CH2Cl2 / 0.25 h / 0 °C 3.2: 78 percent / CH2Cl2 / 12 h 4.1: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C 5.1: 68 percent / HOAt; EDCI; NaHCO3 / CH2Cl2 / 12 h / 0 °C 6.1: 100 percent / aq. LiOH / tetrahydrofuran; methanol / 1.5 h / 25 °C 7.1: HOAt; EDCI / CH2Cl2 / 15 h / -20 °C 7.2: 49 percent / CH2Cl2 / 4 h 8.1: 100 percent / Zn; 90percent aq. AcOH / 2 h / 0 °C 9.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 10.1: Zn; 90percent aq. AcOH / 2 h / 0 °C 11.1: I2 / CH2Cl2; methanol / 2 h / 25 °C 12.1: 3 M HCl / dioxane / 0.5 h / 25 °C 13.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 14.1: TFA; anisole / 6 h / 25 °C 15.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 15.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: HOAt; EDCI / CH2Cl2 / 0.25 h / 0 °C 1.2: 78 percent / CH2Cl2 / 12 h 2.1: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C 3.1: 68 percent / HOAt; EDCI; NaHCO3 / CH2Cl2 / 12 h / 0 °C 4.1: 100 percent / aq. LiOH / tetrahydrofuran; methanol / 1.5 h / 25 °C 5.1: HOAt; EDCI / CH2Cl2 / 15 h / -20 °C 5.2: 49 percent / CH2Cl2 / 4 h 6.1: 100 percent / Zn; 90percent aq. AcOH / 2 h / 0 °C 7.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 8.1: Zn; 90percent aq. AcOH / 2 h / 0 °C 9.1: I2 / CH2Cl2; methanol / 2 h / 25 °C 10.1: 3 M HCl / dioxane / 0.5 h / 25 °C 11.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 12.1: TFA; anisole / 6 h / 25 °C 13.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 13.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: 91 percent / HCl / ethyl acetate / 0.5 h / 25 °C 2.1: HOAt; EDCI / CH2Cl2 / 0.25 h / 0 °C 2.2: 78 percent / CH2Cl2 / 12 h 3.1: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C 4.1: 68 percent / HOAt; EDCI; NaHCO3 / CH2Cl2 / 12 h / 0 °C 5.1: 100 percent / aq. LiOH / tetrahydrofuran; methanol / 1.5 h / 25 °C 6.1: HOAt; EDCI / CH2Cl2 / 15 h / -20 °C 6.2: 49 percent / CH2Cl2 / 4 h 7.1: 100 percent / Zn; 90percent aq. AcOH / 2 h / 0 °C 8.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 9.1: Zn; 90percent aq. AcOH / 2 h / 0 °C 10.1: I2 / CH2Cl2; methanol / 2 h / 25 °C 11.1: 3 M HCl / dioxane / 0.5 h / 25 °C 12.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 13.1: TFA; anisole / 6 h / 25 °C 14.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 14.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 2.1: Zn; 90percent aq. AcOH / 2 h / 0 °C 3.1: I2 / CH2Cl2; methanol / 2 h / 25 °C 4.1: 3 M HCl / dioxane / 0.5 h / 25 °C 5.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 6.1: TFA; anisole / 6 h / 25 °C 7.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 7.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: 100 percent / Zn; 90percent aq. AcOH / 2 h / 0 °C 2.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 3.1: Zn; 90percent aq. AcOH / 2 h / 0 °C 4.1: I2 / CH2Cl2; methanol / 2 h / 25 °C 5.1: 3 M HCl / dioxane / 0.5 h / 25 °C 6.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 7.1: TFA; anisole / 6 h / 25 °C 8.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 8.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: TFA; anisole / 6 h / 25 °C 2.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 2.2: CH2Cl2 / 72 h / 25 °C View Scheme

1.1: 3 M HCl / dioxane / 0.5 h / 25 °C 2.1: HOAt; EDCI / CH2Cl2 / 6 h / 0 °C 3.1: TFA; anisole / 6 h / 25 °C 4.1: DMAP; EDCI / CH2Cl2 / 0.5 h / 25 °C 4.2: CH2Cl2 / 72 h / 25 °C View Scheme