Trimethylsilyldiazomethane → methyl 2-((1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)acetate

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Reaction Steps

To a solution of the product of Step A (436 mg, 0.84 mmol, 1 eq) in methanol (20 mL) at 0° C. was added trimethylsilyl diazomethane (5 mL of a 2 M solution in hexanes, 10 mmol, 11.9 eq) until the yellow color persisted. The yellow solution was concentrated. Purification by chromatography (24 g column) eluting with 40 to 80% EtOAc/heptane afforded the product of Step B. 1H NMR (CHLOROFORM-d) δ: 8.70 (s, 1H), 7.69 (s, 1H), 6.37 (d, J=5.4 Hz, 1H), 5.87 (d, J=5.4 Hz, 1H), 4.98 (d, J=17.4 Hz, 1H), 4.63-4.83 (m, 3H), 4.07-4.20 (m, 1H), 3.79-3.93 (m, 1H), 3.64 (s, 3H), 3.08-3.19 (m, 2H), 3.04 (d, J=15.9 Hz, 1H), 2.62 (dd, J=13.4, 7.1 Hz, 1H), 2.46 (d, J=15.7 Hz, 1H), 2.01-2.12 (m, 1H), 1.43 (s, 9H). Calculated for C23H28F3N3O5: 506.2 (M+23). found: 506.2.

Provenance & Evidence