Methyl 2-(2-aminoethylamino)acetate → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(2-methoxy-2-oxoethylamino)ethylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(2-aminoethylamino)acetate (33.5 mg, 0.254 mmol), Hunig'sBase (0.089 mL, 0.507 mmol) and DMAP (20.66 mg, 0.169 mmol) in DCM (1.5 mL) was added methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (100 mg, 0.169 mmol) in DCM (1.5 mL). The reaction mixture was stirred at 20° C. for three hours. LCMS indicated the formation of desired product. The reaction mixture was quenched with distilled water, extracted with DCM (3×4 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a white solid (90 mg, 76%). LCMS: m/e 713.45 (M−H)−, 2.75 min (method 1).

Provenance & Evidence