Hydrochloric Acid → HCID 86687886, compound

Participants

Reaction Conditions

Reaction Steps

84 mg (0.105 mmol) of N-methyl-L-threonyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-{[(2S)-1-(1,2-oxazinan-2-yl)-1-oxo-3-phenylpropan-2-yl]amino}-3-oxopropyl]-pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide (Example 19) were taken up in 5 ml of dioxane/water (1:1), and 31 μl (0.418 mmol) of a 37% strength aqueous formaldehyde solution and 8 mg (0.126 mmol) of sodium cyanoborohydride were added. Using 1 ml of 0.1 N hydrochloric acid, the mixture was then adjusted to pH 6-7 and stirred at 100° C. for 1 h. The reaction was then poured into a mixture of semisaturated aqueous sodium bicarbonate solution and ethyl acetate. The organic phase was separated off, washed with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue was finally lyophilized from acetonitrile/water. This gave 72 mg (84% of theory) of the title compound in the form of a colourless foam.

Provenance & Evidence