ClC(Cl)(Cl)C(OC(=O)C(Cl)(Cl)Cl)=O.[NH2:14][C:15](=O)[C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[C:15]([C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:23]=1)#[N:14]Trichloroacetic acid anhydride (120 mg, 0.39 mmol) was added slowly to a solution of (S)-tert-butyl 1-amino-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate (50 mg, 0.2 mmol) in methylene chloride (3 mL) and triethylamine (86 uL, 0.62 mmol) at 0° C. The reaction was stirred for 1 h. at 0° C. The reaction was quenched with saturated NaHCO3 and was extracted with ethyl acetate. The organic phase was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) to obtain the (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate (40 mg, 80%) as clear oil. Analytical LCMS (M+Na)+: m/z=327.0.
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