1,1'-Carbonyldiimidazole → n-Hydroxysuccinimide biotin

Biotin (1.0 g, 4.1 mmole) was dissolved in 10 ml DMF (dry) with heating at 80° C. in oil bath. CDI (665 mg, 4.1 mmoles) was added and the mixture was heated at 80° C. The reaction mixture was stirred at 80° C. for 30 minutes, then at room temperature for 2 hours; a white precipitate formed. N-hydroxysuccinimide (475 mg, 4.1 mmoles) was added and the reaction mixture was stirred at room temperature overnight. DMF was removed under vacuum on rotary evaporator. The solid residue was dissolved in 250 ml of refluxing isopropanol, filtered, and stored in the cold room overnight. The precipitate was filtered, washed one time with cold isopropanol and dried in vacuo at 45° C. overnight to give 870 mg (61% yield) of the desired product.

1. temperaturethe mixture was heated at 80° C
2. waitat room temperature for 2 hours
3. customa white precipitate formed
4. stirringthe reaction mixture was stirred at room temperature overnight
5. customDMF was removed under vacuum on rotary evaporator
6. dissolutionThe solid residue was dissolved in 250 ml of refluxing isopropanol
7. filtrationfiltered
8. customstored in the cold room overnight
9. filtrationThe precipitate was filtered
10. washwashed one time with cold isopropanol
11. customdried in vacuo at 45° C. overnight

ORD record

ord-4f78a3a76fa14516a708c8c9afd5f6bd

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04828979