Lithium hydroxide, monohydrate → HCID 53240754, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1R,10R,11S,16S)-3-(methoxycarbonyl)-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (84) (0.1 g, 0.2 mmol) and LiOH.H2O (0.1 g, 4 mmol) in MeOH (5.0 mL) and water (5.0 mL) was heated at 90° C. for 72 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and acidified with 1 M HCl. The resulting solid was collected by filtration to give (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo-[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3,5-dicarboxylic acid (85) (0.09 g, 94%) as a white solid. 1H NMR (CD3OD): δ 8.43 (d, 1H), 8.07 (d, 1H), 3.56 (m, 2H), 2.92 (d, 1H), 2.18 (d, 1H), 1.90-1.38 (m, 11H), 1.30-1.17 (m, 2H), 1.08-0.96 (m, 5H), 0.90 (s, 3H), 0.87 (s, 3H). MS m/z 433 (O23H30O6S−H+).

Provenance & Evidence