Methanol → HCID 67178737, compound

Participants

Reaction Conditions

Reaction Steps

Following a method analogous to General Procedure C, a portion of the above crude alpha-bromoketone (81 mg, 0.37 mmol) was added to a methanol (about 10 mL) solution of 3-[1-(5-ethyl-thiophen-2-ylmethyl)-thioureido]-propionic acid tert-butyl ester (122 mg, 0.371 mmol) and the reaction was heated at 60° C. and stirred overnight. The solvent was evaporated and ethyl acetate and saturated aq sodium bicarbonate solution were added to the residue. Extraction of the aq layer was performed two times with ethyl acetate. The combined organic portion was dried over sodium sulfate, and the dried solvent was decanted from the drying agent. The solvent was removed under reduced pressure to give the crude material. This was purified using silica gel chromatography (eluent: hexanes→19:1 hexanes:EtOAc→9:1 hexanes:EtOAc to give the purified 3-[(4-bicyclo[2.2.1]hept-2-yl-thiazol-2-yl)-(5-ethyl-thiophen-2-ylmethyl)-amino]-propionic acid tert-butyl ester (139 mg, 0.311 mmol, 84%) after evaporation of the eluent under reduced pressure.

Provenance & Evidence