1,2-Dichloroethane → HCID 86692353, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-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)cyclohex-3-enecarboxylic acid (0.1 g, 0.144 mmol) in dichloromethane (4 mL) was added thionyl chloride (0.105 mL, 1.439 mmol). The mixture was attached to a reflux condensor and was heated to reflux. The solids did not completely dissolve, so DCE (3 mL) was added and the mixture was warmed to 60° C. with a reflux condensor attached. Solids still remained, so THF (2 mL) was added and the mixture was further heated to 70° C. The solids never completely dissolved, but the reaction was allowed to reflux regardless. After 4 h of heating, the mixture was cooled to rt. LC/MS showed the methyl ester since methanol was added to analytical sample to help solubilize the product for analysis. The mixture was concentrated under reduced pressure, then was diluted with dichloromethane and concentrated two additional times. The crude product was used in the next step with no additional purification. LCMS: m/e 709.7 (M+MeOH)+, 2.08 min (method 1).

Provenance & Evidence