Water → HCID 57504475, compound

Participants

Reaction Steps

A stirred solution of 2-bromo-4-(2-methoxyethoxy)butanoic acid (Step 4) (200 mg, 0.83 mmol) in thionyl chloride (4 mL) was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo to remove excess thionyl chloride. The residue was dissolved in DCM (2 mL) and was added slowly to a stirred solution of 2-amino-4-methylthiazole (99.5 mg, 0.871 mmol) and DIPEA (117.9 mg, 0.913 mmol) in DCM (4 mL). The reaction mixture was kept at ambient temperature for 1 h before water was added and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:1/1) to give the title compound as an oil (105 mg), 1H NMR (300 MHz, CDCl3) δ 6.57 (d, 1H), 4.72 (dd, 1H), 3.66 (m, 2H), 3.60 (m, 2H), 3.51 (m, 2H), 3.36 (s, 3H), 2.50 (m, 1H), 2.31 (m, 4H).

Provenance & Evidence