Cyclohexyl isocyanide → 7-Bromo-4-(2,6-difluoro-benzyl)-2-ethyl-3-oxo-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine-5-carboxylic acid cyclohexylamide

関与物質

反応手順

2,6-Difluorobenzylamine (51 mg, 0.35 mmol) and cyclohexylisocyanide (39 mg, 0.36 mmol) were added to a solution of 2-(4-bromo-2-formyl-phenoxy)-butyric acid (prepared in analogy to 2-(4-bromo-2-formyl-phenoxy)-3-methyl-butyric acid [example 1] from ethyl 2-bromo-3-methyl butyrat, 100 mg, 0.35 mmol) in methanol (0.5 ml). After stirring for 2 h at r.t., the title compound was isolated (diastereomer 1 [inhibitorially active], retention time 2.09 min: 17.9 mg; diastereomer 2 [inhibitorially active], retention time 2.28 min, 7.3 mg, combined yield 14%, MS: m/e=521.1 [M+H+]) from the reaction mixture by reversed-phase, preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5–95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

情報源と証拠