Benzyl 6-[(tert-butoxycarbonyl)amino]-2-methyl-3-vinylbenzoate → 6-[(Tert-butoxycarbonyl)amino]-3-ethyl-2-methylbenzoic acid

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Reaction Steps

A mixture of Example 145A (450 mg, 1.2 mmol), palladium hydroxide (540 mg), and methanol (150 mL) was heated to 50° C. in a Paar shaker under 65 psi hydrogen pressure for 72 hours. The mixture was filtered, concentrated, and purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min to provide the desired product. MS (ESI(+)) m/e 280 (M+H)+, 297 (M+NH4)+, 302 (M+Na)+; (ESI(−)) m/e 278 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 13.28 (br s, 1H), 8.35 (s, 1H), 7.32 (d, 1H), 7.17 (d, 1H), 2.58 (q, 2H), 2.24 (s, 3H), 1.43 (s, 9H), 1.12 (t, 3H).

Provenance & Evidence