Boron tribromide → N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trihydroxy-benzamide

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Reaction Steps

A procedure similar to that in Example 7 was used. N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide prepared in Example 50 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with acetone to obtain a product as a white solid in a yield of 55.8%, mp: 238-239 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.80˜0.90 (2H, m), 1.00˜1.23 (3H, m), 1.45˜1.75 (6H, m), 2.70 (2H, d, J=7.00 Hz, CHCH2Ar), 6.84 (2H, d, J=8.68 Hz, ArH), 7.09 (2H, s, ArH), 7.38 (2H, d, J=8.68 Hz, ArH), 9.17 (4H, br, 4×OH), 12.20 (1H, br, CONH); EI-MS m/e (%): 440.0 (M+, 6), 288.1 (38), 205.1 (100), 163.0 (28); HREI-MS Calcd. for C23H24N2O5S: 440.1406. found: 440.1406.

Provenance & Evidence