Sodium Hydroxide → 4-[3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acid

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Reaction Steps

A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acid ethyl ester (Example 3j, 1.34 g, 3.29 mmol) and aqueous sodium hydroxide (2N, 20 mL) in tetrahydrofuran (20 mL) and methanol (20 mL) is refluxed for 1 hour. The solution is partially concentrated in vacuo, then acidified to pH 6 and extracted with chloroform. The combined organic extracts are dried over Na2SO4, filtered, and concentrated to give the title compound (1.40 g). 1H NMR (CDCl3): δ 7.59 (dd, 1H), 6.06 (dd, 1H), 4.80–4.70 (bd, 1H), 4.38–4.22 (m, 1H), 3.79–3.50 (m, 3H), 3.47–3.35 (m, 1H), 2.98–2.87 (m, 1H), 2.30–2.14 (m, 1H), 1.97–1.84 (m, 1H), 1.46 (s, 9H), 0.69–0.54 (m, 4H).

Provenance & Evidence