N-Boc-N-methylethylenediamine → methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(tert-butoxycarbonyl(methyl)amino)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 Steps

To a mixture of tert-butyl 2-aminoethyl(methyl)carbamate (17.68 mg, 0.101 mmol), Hunig'sBase (0.053 mL, 0.304 mmol) and DMAP (1.240 mg, 10.15 μmol) in DCM (1 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 (60 mg, 0.101 mmol) in DCM (1 mL). The reaction mixture was stirred for 1 hour. LCMS indicated the formation of desired product. The reaction mixture was quenched with distilled water, extracted with DCM (3×3 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the desired product as white solid (65 mg, 88%). LCMS: m/e 729.61 (M+H)+, 2.72 min (method 1).

Provenance & Evidence