Methylamine → (1R,10S,11S,16S)-3-methoxy-N,11,15,15-tetramethyl-8,8-dioxo-8lambda6thiatetracyclo[8.8.0.02,7.011,16]-octadeca-2,4,6-triene-5-carboxamide

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Reaction Steps

A mixture of (1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (61) (0.35 g, 0.83 mmol), HATU (0.61 g, 1.7 mmol), N-methylmorpholine (0.18 mL, 2.5 mmol), methylamine (2 M in THF, 1.04 mL, 2.08 mmol), THF (10.0 mL) and DMF (2.0 mL) in a sealed tube was stirred at room temperature for 18 h. The THF was evaporated and the residue was quenched with water. The resulting solid was collected by filtration. The crude product was purified by flash chromatography on silica gel (Hexanes/EtOAc, 1:1) to yield (1R,10S,11S,16S)-3-methoxy-N,11,15,15-tetramethyl-8,8-dioxo-8λ6thiatetracyclo[8.8.0.02,7.011,16]-octadeca-2,4,6-triene-5-carboxamide (0.26 g, 74%) (Compound No. 62) as a white solid. 1H NMR (CDCl3): δ 8.77 (s, 1H), 8.07 (s, 1H), 7.60 (s, 1H), 6.59 (m, 1H), 3.52 (m, 1H), 3.37 (m, 1H), 3.24 (m, 1H), 3.05 (d, 3H), 2.32 (d, 1H), 1.65-1.10 (m, 13H), 0.97 (s, 3H), 0.88 (s, 3H), 0.84 (s, 3H). MS m/z 420 (C23H33NO4S+H+).

Provenance & Evidence