PMC:7571312 / 90595-91590 JSONTXT

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{"target":"https://pubannotation.org/docs/sourcedb/PMC/sourceid/7571312","sourcedb":"PMC","sourceid":"7571312","source_url":"https://www.ncbi.nlm.nih.gov/pmc/7571312","text":"To a solution of N-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-methyl-l-norleucine (2.14 g, 5.8 mmol) in methanol (15 mL) is added toluene (30 mL) followed by the dropwise addition of TMS-diazomethane (2.9 mL, 2 M in hexane, 5.8 mmol). TLC analysis indicated incomplete reaction, and TMS-diazomethane was added dropwise until a yellow color persisted. At this time, the reaction was quenched by the addition of AcOH (1 mL) followed by concentration in vacuo. The residue was purified by Biotage flash chromatography, eluting with ethyl acetate/hexane to afford the title compound as a white solid, 2.18 g, 98%. 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J = 7.6 Hz, 2H), 7.60 (dd, J = 7.2, 3.9 Hz, 2H), 7.40 (t, J = 7.2 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 5.26 (d, J = 8.6 Hz, 1H), 4.31–4.51 (m, 3H), 4.23 (t, J = 7.1 Hz, 1H), 3.75 (s, 3H), 1.78–1.93 (m, 1H), 1.60–1.76 (m, 1H), 1.45–1.60 (m, 1H), 1.05–1.34 (m, 2H), 0.88 (d, J = 4 Hz, 3H), 0.86 (d, J = 4 Hz, 3H); MS (APCI+) for C23H27NO4m/z 160.1 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