Diisopropylethylamine → HCID 141603152, compound

Participants

Reaction Steps

A solution of Compound 15 (0.94 g, 2.97 mmol), N,N′-bis-(tert.-butoxycarbonyl)-S-methylisothiourea (0.92 g, 3.17 mmol) and N-ethyldiisopropylamine (0.58 ml, 3.33 mmol) in absolute N,N-dimethylformamide (40 ml) was mixed with silver nitrate (0.54 g, 3.18 mmol) and the mixture stirred for 4 hours. Then the silver mercaptane was filtered off through Celite and washed afterwards with CH2Cl2 (4×50 ml). The filtrate was washed with H2O (10×150 ml) and saturated NaCl solution (2×150 ml), dried (Na2SO4) and evaporated. In this way 1.46 g of a yellow foam resin was obtained which was purified through MPLC (p=5 bar, silica gel 60, CH2Cl2/MeOH/conc. ammonia 95:4, 5:0.5). Yield: 0.77 g (46%) of green foam resin: 1H-NMR (CDCl3): δ 11.49 (s, br, NH—COO(CH3)3); 8.59 (d, J=8.0, C(6)-NH—); 6.71 (d, J=8.4, 1 arom. H); 6.56 (d, J=8.4, 1 arom. H); 4.41 (d, J=7.2, H—C(5)); 3.22 (s, CH3O—C(14)); 2.38 (s, CH3N); 1.51 (s, C(CH3)3), 1.47 (s, C(CH3)3).

Provenance & Evidence