Triethylamine → 2-Acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-pyridin-4-yl)-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]=1)=[CH2:6])[CH3:2].C(N(CC)CC)C.[C:30]([OH:33])(=[S:32])[CH3:31]>>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([CH2:6][S:32][C:30](=[O:33])[CH3:31])[CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:9]=1)[CH3:2]Participants
4
Procedure
A solution of 2-(2-tert-butoxycarbonylamino-pyridin-4-ylmethyl)-acrylic acid ethyl ester (0.48 g, 1.57 mmol) and triethylamine (0.17 g, 1.64 mmol) was added to thioacetic acid (3 mL) at 0° C. under nitrogen. The mixture was stirred at room temperature for 4 h. The mixture was poured onto ice-water and extracted with CH2Cl2. The organic phase was washed with saturated NaHCO3 (aq) and dried. The crude product was purified by flash chromatography (2.5% MeOH in CH2Cl2) to give 2-acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-pyridin-4-yl)-propionic acid ethyl ester (0.60 g, 100%).