4-Methylmorpholine → HCID 53240856, compound

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Reaction Steps

A mixture of (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-triene-3-carboxylic acid (65) (0.20 g, 0.49 mmol), HATU (0.37 g, 0.98 mmol), N-methylmorpholine (0.10 mL, 1.5 mmol) and 1-methyl piperazine (0.15 mL, 1.5 mmol) in THF (10 mL) and DMF (2.0 mL) was stirred at room temperature for 18 h. The THF was evaporated under reduced pressure, the residue was quenched with water and the resulted solid was collected by filtration. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH, 10:1). The resulting material was further purified by preparative HPLC (NH4OAc/CH3CN) to give (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-3-[(4-methylpiperazin-1-yl)carbonyl]-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (94) (0.085 g, 34%) as a white solid. 1H NMR (CDCl3): δ 7.29 (d, 1H), 6.77 (d, 1H), 3.62-3.20 (m, 5H), 2.70-2.00 (m, 10H), 1.78-1.24 (m, 10H), 1.20-1.00 (m, 2H), 0.99-0.92 (m, 4H), 0.88 (s, 3H), 0.82 (s, 3H). MS m/z 489 (C27H40N2O4S+H+).

Provenance & Evidence