Pyridine → toluene-4-thiosulfonic acid S-(4,5-bis-tert-butoxycarbonylamino-2-tert-butyl-phenyl)ester

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Reaction Steps

The title compound was prepared according to the General Method 15 using (2-tert-butoxycarbonylamino-4-tert-butyl-5-mercapto-phenyl)-carbamic acid tert-butyl ester (prepared in Example TT-2; 16.9 g, 42.8 mmol), tosyl bromide (10.04 g, 42.76 mmol), pyridine (10 mL), and EtOAc (150 mL). The crude product was purified by flash chromatography (5%-60% EtOAc in hexanes as eluents). 1 H-NMR (CDCl3): δ1.19 (s, 9 H), 1.53 (s, 18 H), 2.42 (s, 3 H), 6.42 (br s, 1 H), 7.22 (d, 2 H), 7.28 (s, 1 H), 7.5 (m, 3 H), 7.87 (br s, 1 H).

Provenance & Evidence