Ethanolamine → Fucose n-Decyl Acrylamide

A solution was prepared of poly(N-acryloyloxysuccinimide)(pNAS; 1.5 g, 8.87 mmol) in dimethylformamide (DMF, 60 mL). To this solution was added triethylamine (1.5 mL), followed by the dropwise addition of the L-fucose derivative 1 (667 mg, 2.21 mmol, 25 mol % with respect to pNAS). The solution was stirred at room temperature for 12 h, and subsequently heated to 40° C. for 24 h. The solution was cooled and n-decylamine (138 mg, 20 mol % with respect to pNAS) was added as a solution in DMF (1 mL). The solution was stirred at 40° C. for a further 24 h, followed by the addition of ethanolamine (2 mL, excess as a solution in 5 mL of DMF). The reaction mixture was stirred for 243 h at 40° C., cooled and precipitated into acetone (300 mL). The polymer was recovered by centrifugation, washed with acetone (10 mL) and the finely divided white solid dissolved in deionized water (10 mL) and dialysed against water for 24 h. The clear solution was lyophilized to dryness to give the desired product in 72% yield.

1. temperaturesubsequently heated to 40° C. for 24 h
2. temperatureThe solution was cooled
3. stirringThe solution was stirred at 40° C. for a further 24 h
4. stirringThe reaction mixture was stirred for 243 h at 40° C.
5. temperaturecooled
6. customprecipitated into acetone (300 mL)
7. customThe polymer was recovered by centrifugation
8. washwashed with acetone (10 mL)
9. dissolutionthe finely divided white solid dissolved in deionized water (10 mL)
10. customdialysed against water for 24 h

ORD record

ord-eead5ec383ad4371a36d07efcf8bffee

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05891862