Hydrochloric Acid → HCID 86622312, compound

Participants

Reaction Steps

Step I (1): DIEA (436 μL, 3.2 mmol) was added to a solution of (S)-methyl 2-(methylamino)pent-4-enoate hydrochloride (229 mg, 1.28 mmol) and 3,3,3-trifluoropropane-1-sulfonyl chloride (250 mg, 1.28 mmol) in DCM. The reaction mixture was stirred for 24 h at rt. The resulting solution was poured into 1 N HCl and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography (1-50% EtOAc/hexanes, linear gradient) to afford 288 mg (74% yield) of (S)-methyl 2-(3,3,3-trifluoro-N-methylpropylsulfonamido)pent-4-enoate as a viscous oil. LC-MS (M+H)+=303.9; 1H NMR (500 MHz, CDCl3) δ ppm 2.42-2.51 (m, 1H) 2.58-2.69 (m, 2H) 2.73-2.81 (m, 1H) 2.87 (s, 3H) 3.17-3.29 (m, 2H) 3.77 (s, 3H) 4.63 (dd, J=10.53, 5.34 Hz, 1H) 5.13-5.23 (m, 2H) 5.70-5.83 (m, 1H).

Provenance & Evidence