Triethylamine → tert-Butyl 3-((3,5-dichloro-N-(4-(4-fluorophenoxy)benzyl)-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-((4-(4-fluorophenoxy)benzylamino)methyl)benzylcarbamate (0.72 g, 1.64 mmol) in CH2Cl2 (15 mL) added 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (0.45 g, 1.72 mmol) and Et3N (0.68 ml, 4.91 mmol). The reaction mixture was stirred at 0° C. under nitrogen for 1.5 h. The reaction mixture was concentrated and the residue was extracted with ethyl acetate and saturated NaHCO3 solution. The organic layer was washed successively with brine, 1 N HCl, brine, and concentrated after drying over MgSO4 to give viscous solid (0.99 g, 82%). 1H NMR (CDCl3): δ 9.10 (bs, 1H), 7.52 (d, J=2.8 Hz, 1H), 7.40 (d, J=2.8 Hz, 1H), 7.28-7.17 (m, 1H), 7.14-6.90 (m, 9H), 6.85 (d, J=8.3 Hz, 2H), 4.36 (m, 4H), 4.23 (m, 2H), 1.46 (s, 9H); MS (ESI): (M+H)+=605.2.

Provenance & Evidence