Triethylamine → tert-butyl N-[4-[3-[2-[(2-bromoacetyl)amino]-4-methoxy-6-methylphenyl]phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Participants

Reaction Steps

Following the procedure described for Example 234, step a, reaction of {[4-(6′-amino-4′-methoxy-2′-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (204 mg, 0.37 mmol, as prepared in Example 198, step e), bromoacetyl bromide (39 μL, 0.45 mmol), and Et3N (77 μL, 0.56 mmol) in DCM (5 mL) afforded 170 mg (69%) of the title compound as a yellow foamy solid after chromatography (PTLC, 50% EtOAc in hexanes, 4×1000μ SiO2 plate). 1H-NMR (CDCl3; 400 MHz): δ 8.02–8.05 (m, 1H), 7.91 (s, 1H), 7.87 (t, 1H, J=1.6 Hz), 7.73 (br s, 1H), 7.63–7.67 (m, 2H), 7.45–7.49 (m, 1H), 6.69 (d, 1H, J=2.1 Hz), 3.85 (s, 3H), 3.69 and 3.74 (AB quartet, 2H, J=14.1 Hz), 2.59 (s, 3H), 2.00 (s, 3H), 1.52 (s, 9H). ESI-MS (m/z): Calcd. for C27H30BrN3O6S3: 668.0 (M+H); found: 669.6, 667.6, 570.0, 568.0 (M−Boc).

Provenance & Evidence