Dichloromethane → (2R,3R,4S,5R,6E)-7-(2-bromophenyl)-3,4,5-trihydroxy-2-methoxy-N-[(3S)-5-methyl-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepin-3-yl]hept-6-enamide

Participants

Reaction Steps

90 mg of 45 (0.22 mmol), 51 mg of 6 (0.22 mmol) and 93 mg of sodium 2-ethylhexanoate (0.56 mmol) in 2.0 mL of THF are successively introduced into a 10 mL round-bottomed flask, with stirring and under an argon atmosphere. The stirring is maintained at RT for 24 h. 20 mL of CH2Cl2 are added to the reaction medium. The mixture is successively washed with 10 mL of an HCl solution (1N), 10 mL of water saturated with NaCl. The organic phase is dried over anhydrous magnesium sulphate, filtered and then evaporated to dryness. The crude product is chromatographed on a silica cartridge (9 g, eluent, AcOEt/heptane:85/15). 49 mg of expected product Ex18 (white solid) are recovered.

Provenance & Evidence