Cl.[NH2:2][CH2:3][CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].C1COCC1.CCN(C(C)C)C(C)C.O([CH2:38][C:39]([F:42])([F:41])[F:40])S(C(F)(F)F)(=O)=O>CN(C=O)C>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH:4]([CH2:3][NH:2][CH2:38][C:39]([F:42])([F:41])[F:40])[C:5]([O:7][CH3:8])=[O:6])=[CH:14][CH:13]=1A solution of methyl 3-amino-2-(4-chlorophenyl)propanoate hydrochloride (215 mg, 0.86 mmol) in 1:1 THF:DMF (3.0 mL) was treated with DIEA (389 uL, 2.23 mmol) at room temperature. Trifluoroethyl triflate (299 mg, 1.29 mmol) was added to the mixture, and the reaction was stirred for 20 hours to completion. The mixture was partitioned between ethyl acetate and diluted NaHCO3 solution. The aqueous portion was extracted twice, and the combined organic portions were washed with water (3×). The organic portion was washed with brine, separated, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography (silica gel eluted with 4:1 hexanes:ethyl acetate, Rf=0.18) to afford the pure methyl 2-(4-chlorophenyl)-3-(2,2,2-trifluoroethylamino)propanoate (235 mg, 93%) as a colorless oil. LCMS (APCI+) m/z 296.0 [M+H]+.
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