Hydrochloric Acid → HCID 11752505, compound

Participants

Reaction Conditions

Reaction Steps

To a chilled (0° C.) solution of 130 mg (0.25 mmol) of 3-amino-5-methyl-4-[5,5,5-trifluoro-4-hydroxy-4-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-1-ynyl]benzonitrile in 5 mL of dichloromethane was added 105 μL (0.74 mmol) of trifluoroacetic anhydride. After 15 minutes, the reaction was concentrated in vacuo and the residue was diluted with diethyl ether and concentrated in vacuo, three times. The resulting oil was dissolved in 1 mL of DMSO and then 0.09 mL (0.74 mmol) of tetramethylguanidine was added and the mixture was warmed at 140° C. in a microwave oven. After 10 minutes, the mixture was cooled, poured onto crushed ice with 1N aqueous HCl and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by preparatory TLC (silica gel, 1:1 ethyl acetate-hexanes) to afford first 35 mg (27%) of the title compound as a single diastereomer (M−1=505) and second 10 mg (8%) of the title compound as the opposite diastereomer (M−1=505).

Provenance & Evidence