Potassium Carbonate → HCID 67431557, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,2S)-2-thiophen-2-yl-cyclopropanecarboxylic acid [(R)-2-hydroxy-1-[4-hydroxy-phenyl)-ethyl]-amide (35 mg, 0.105 mmol) dissolved in 0.8 mL DMF was added the 2-ethylbutyl bromide (38 mg, 0.231 mmol) followed by K2CO3 (32 mg, 0.231 mmol). It was heated to 60° C. with stirring overnight. On the next day it was cooled to rt, diluted with ether and quenched with water. The organic layer was washed with water and brine, dried over MgSO4, and concentrated. It was then purified by flash column (20-40% EtOAc in DCM) to afford the titled compound (26 mg, 58%). 1H NMR (400 MHz, MeOD) δ ppm 5.8 (d, J=8.6 Hz, 2 H), 5.7 (dd, J=5.2, 1.1 Hz, 1H), 5.4 (d, J=8.6 Hz, 3H), 5.3 (d, J=3.5 Hz, 1H), 3.4-3.5 (m, 1H), 2.4 (d, J=5.6 Hz, 2H), 2.2 (dd, J=6.6, 3.0 Hz, 2H), 1.0 (dd, J=6.3, 2.5 Hz, 1H), 0.5 (ddd, J=8.6, 4.7, 4.4 Hz, 1H), 0.1-0.2 (m, 1H), −0.1-0.1 (m, J=15.1, 7.7, 7.6, 7.6 Hz, 5H), −0.2 (ddd, J=8.5, 6.2, 4.3 Hz, 1H), −0.5 (t, J=7.5 Hz, 6H). LRMS (ESI)=388, [(M+1)+ calcd for C22H30NO3S 387.5].

Provenance & Evidence