THF TFA water → N-(2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepin-4-yl)-(E)-(2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8,8-dimethylnon-6-enamide

Participants

Reaction Conditions

Reaction Steps

24 mg (50 μmol) of product 5, and then 2 ml of a cold trifluoroacetic acid/tetrahydrofuran/water mixture (1.6/1.6/1.0 v/v/v) are successively introduced, at 0° C., into a round-bottomed flask equipped with a magnetic stirrer. This mixture is maintained at 0° C. until the starting material has disappeared on TLC (1 hour) (90/10 v/v dichloromethane/methanol). The solvent is evaporated off under reduced pressure and 2 ml of methanol are added to the residue, which is reevaporated under reduced pressure. This last step is repeated a second time and the residue is dissolved in 5 ml of water in a minimum volume of methanol (0.5 ml). The solution is freeze-dried, giving the expected product Example 1 quantitatively in the form of a foam.

Provenance & Evidence