tert-Butanol → HCID 67538549, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.53 mL, 3.81 mmol) was added to a solution of 2-(4-chlorophenyl)-2-fluoro-pentanedioic acid 1-ethyl ester (1.00 g, 3.46 mmol) in t-BuOH (20 mL) followed by the addition of diphenylphosphoryl azide (0.82 mL, 3.81 mmol). The mixture was heated at 95° C. for 3 hours, concentrated in vacuo, and partitioned between dilute aqueous NaHCO3 and DCM. The separated DCM layer was dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed (SiO2) using DCM as eluent to give 4-tert-butoxycarbonylamino-2-(4-chlorophenyl)-2-fluoro-butyric acid ethyl ester (600 mg). 1H NMR (CDCl3, 400 MHz) δ 7.42 (m, 2H), 7.35 (m, 2H), 5.25 (m, 0.4H), 4.61 (m, 0.6H), 4.19 (m, 2H), 3.35 (m, 0.6H), 3.23 (m, 1.4H), 2.59 (m, 1H), 2.34 (m, 1H), 1.40 (m, 9H), 1.24 (m, 3H). LCMS (APCI+) m/z 260 [M+H]+(loss of Boc group).

Provenance & Evidence