Trifluoroacetic acid → HCID 53240949, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-{[(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]-carbonyl}piperazine-1-carboxylate (99) (0.13 g, 0.23 mmol) and trifluoroacetic acid (1.0 mL, 13 mmol) in CH2Cl2 (10 mL) was stirred at room temperature under N2 for 18 h. The mixture was concentrated under reduced pressure, and basified with Et3N, dissolved in EtOAc and washed with water. The organic layer was separated and concentrated to dryness under reduced pressure to give (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-3-[(piperazin-1-yl)carbonyl]-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (100) (0.06 g, 55%) as a brown solid. 1H NMR (CD3OD): δ 7.27 (d, 1H), 6.78 (d, 1H), 3.50 (m, 3H), 3.02 (m 2H), 2.90 (m, 2H), 2.53 (m, 1H), 2.16 (d, 1H), 1.88-1.14 (m, 14H), 1.00 (m, 5H), 0.90 (s, 3H), 0.86 (s, 3H). MS m/z 475 (C26H38N2O4S+H+).

Provenance & Evidence