Lithium hydroxide, monohydrate → HCID 53240854, compound

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A mixture of methyl 2-{[(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl]formamido}acetate (90) (0.13 g, 0.27 mmol) and LiOH.H2O (0.07 g, 2 mmol) in MeOH (10 mL) and water (10 mL) was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure and the aqueous residue was acidified with 1 M HCl. The resulting solid was collected by filtration to give 2-{[(1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl]formamido}acetic acid (91) (0.09 g, 72%) as a brown solid. 1H NMR (CD3OD): δ 8.82 (m, 1H), 7.24 (d, 1H), 7.03 (d, 1H), 4.06 (m, 2H), 3.47 (m 2H), 2.76 (d, 1H), 2.11 (d, 1H), 1.88-1.38 (m, 10H), 1.20 (m, 1H), 1.00 (m, 5H), 0.89 (s, 3H), 0.86 (s, 3H). MS m/z 464 (C24H33NO6S+H+).

Provenance & Evidence