Triethylamine → tert-butyl 3-((N-(biphenyl-4-ylmethyl)-3,5-dichloro-2-hydroxyphenylsulfonamido)methyl)benzylcarbamate

Participants

Reaction Steps

To a solution of tert-butyl 3-((biphenyl-4-ylmethylamino)methyl)benzylcarbamate (2.42 g, 6.01 mmol) in CH2Cl2 (30.0 mL) was added a solution of 3,5-dichloro-2-hydroxybenzene-1-sulfonyl chloride (1.65 g, 6.31 mmol) in CH2Cl2 (8.0 mL) at ice bath temperature followed by Et3N (2.5 mL, 18.0 mmol). The reaction mixture was stirred at ice bath temperature for 1.5 h and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 eluting with CH2Cl2 to 8% of ethyl acetate in CH2Cl2 to give the product as a white glassy solid (2.78 g, 72.5%). 1H NMR (CDCl3): δ 9.18 (bs, 1H), 7.59-7.38 (m, 9H), 7.28-7.21 (m, 4H), 7.06 (m, 2H), 4.48 (s, 2H), 4.43 (s, 2H), 4.25 (s, 2H), 1.49 (s, 9H).

Provenance & Evidence