Water → HCID 59382941, compound

Participants

Reaction Steps

To a solution of tert-butyl (S)-1-(2,2,2-trifluoroethylamino)-3-cyclohexylpropan-2-ylcarbamate (1.7 g, 5 mmol) and Et3N (2 mL, 15 mmol) in CH2Cl2 (20 mL) was added dropwise a solution of CbzCl (1.02 g, 6 mmol) in CH2Cl2 (10 mL) at 0° C. After stirring for an additional 2 h, water (30 mL) was added. The mixture was extracted with CH2Cl2 (2×20 mL), the organic layers were washed with brine, dried over MgSO4, and evaporated. The residue was purified by silica chromatography to obtain benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-propyl-2,2,2-trifluoroethylcarbamate (250 mg, yield 10% for 2 steps) as an oil. 1H NMR (CDCl3, 400 MHZ) δ 0.90 (m, 2 H), 1.25 (m, 4 H), 1.44 (s, 9 H), 1.70 (m, 7 H), 3.33 (m, 2 H), 3.85 (m, 3 H), 4.45 (brs, 1 H), 5.20 (s, 2 H), 7.36 (m, 5 H).

Provenance & Evidence