Diisopropylethylamine → HCID 141603155, compound

Participants

Reaction Steps

A solution of Compound 13 (1.00 g, 3.16 mmol), N,N′-bis-(tert.-butoxycarbonyl)-S-methylisothiourea (1.00 g, 3.44 mmol) and N-ethyldiisopropylamine (0.60 ml, 3.44 mmol) in absolute N,N-dimethylformamide (60 ml) was mixed with silver nitrate (0.55 g, 3.24 mmol) and the mixture stirred for 1.5 h. Then the silver mercaptane was filtered off through Celite and washed afterwards with CH2Cl2 (4×50 ml). The filtrate was washed with H2O (6×200 ml) and saturated NaCl solution (1×200 ml), dried (Na2SO4) and evaporated. In this way 1.85 g of a yellow oil were obtained which was purified through MPLC (p=5 bar, silica gel 60, CH2Cl2/MeOH 10:1). Yield: 0.67 g (38%) of white foam resin: 1H-NMR (CDCl3): δ 11.53 (s, br, NH—COO(CH3)3); 8.81 (d, J=8.0, C(6)-NH—); 6.73 (d, J=8.2,1 arom. H); 6.56 (d, J=8.2, 1 arom. H); 4.66 (dd, 3J=2.6, 4J=1.6, H—C(5)); 3.25 (s, CH3O—C(14)); 2.35 (s, CH3N); 1.50 (s, 2×C(CH3)3).

Provenance & Evidence