Acryloyl chloride → N-Acryloyl-D-glucamine

Participants

Reaction Steps

1-Amino-1-deoxy-D-sorbitol (D-glucamine) 10 (5.0 g, 28 mmol) was dissolved in a mixture of CH3OH (120 mL) and H2O (15 mL) and cooled in an ice bath. Acryloyl chloride (30 mL of a 2.35 M solution in THF, 71 mmol) was added dropwise to. the above solution, while the pH of the reaction mixture was maintained between 8 and 9 by periodic addition of 2M aqueous KOH. After an additional 1-h period on ice, the volatiles were evaporated under reduced pressure and the residue was subjected to silica gel chromatography with a gradient of 5-15% CH2Cl2 in MeOH to give 3.6 g (56%) compound 3 as a white solid; mp 122-123° C.

Provenance & Evidence