Water → HCID 58391157, compound

Participants

Reaction Steps

To a solution of the compound obtained in example 15.1 (0.2 mmole, 90 mg) in dichloromethane (8 mL), kept under stirring, were added acetic anhydride (1 mmole, 94 μL), pyridine (0.5 mmole, 40 μL) and a catalytic amount of DMAP. Stirring was continued for 3 hours. At the end the reaction mixture was diluted with H2O (10 mL) and extracted with dichloromethane (2×5 mL). The organic phases were pooled and washed, in the order, with a NaHCO3 saturated aqueous solution (1×10 mL), with a 1N aqueous solution of HCl (1×10 mL) and with brine (1×10 mL). The organic phase were dried over Na2SO4, filtered and concentrated under vacuum to give 92 mg (93% yield) of (1R,3R)-3-((2S,3S)-2-azido-N-(2-methoxyethyl)-3-methylpentanamido)−4−methyl-1-(4-(methylcarbamoyl)thiazol-2-yl)pentyl acetate. Rf=0.32 (petroleum ether/ethyl acetate 1/1 volume/volume).

Provenance & Evidence