Hydrochloric Acid → N-(4-aminooxybutyl)biotinamide

To a solution of ethyl N-[(4-biotinamidobutyl)oxy]acetimidate (4) (0.4 g, 1.0 mmol) in 25 mL of absolute ethanol in a 50 mL round bottom flask fitted with a reflux condenser was added 0.2 mL of concentrated aqueous hydrochloric acid and the solution was stirred and refluxed for 1 hour. The solvents were removed on a rotary evaporator and the residue was azeotroped with four successive 20 mL volumes of absolute ethanol. Deionized water (20 mL) was added to the crude product and the solution was filtered and the solid discarded. A solution of 0.1N aqueous sodium carbonate was added to the filtrate to bring the pH to 8.0 and the solution was reduced to dryness on a rotary evaporator. The white solid, which contained some sodium carbonate, was treated with 5 mL of absolute ethanol, which dissolved the organic material and filtered to remove sodium carbonate. This procedure was repeated twice more to yield 202 mg (60%) of N-(4-aminooxybutyl)-biotinamide (V). Single spot on TLC (85:15 chloroform:methanol) Rf =0.14. m.p. 168° C.-170° C. 1H NMR (DMSO-d6): δ7.8 (m, 1H), 6.4 (s, 1H), 6.3 (s, 1H), 5.7 (s, 2H), 4.3 (m, 1H), 4.1 (m, 1H), 3.4(t, 2H), 2.9-3.2 (m, 4H), 2.7 (dd, 2H), 2.5 (d, 2H), 2.0 (t, 2H), 1.2-1.7 (m, 8H).

1. temperaturerefluxed for 1 hour
2. customThe solvents were removed on a rotary evaporator
3. customthe residue was azeotroped with four successive 20 mL volumes of absolute ethanol
4. additionDeionized water (20 mL) was added to the crude product
5. filtrationthe solution was filtered
6. additionA solution of 0.1N aqueous sodium carbonate was added to the filtrate
7. customthe solution was reduced to dryness on a rotary evaporator
8. additionwas treated with 5 mL of absolute ethanol, which
9. dissolutiondissolved the organic material
10. filtrationfiltered
11. customto remove sodium carbonate

ORD record

ord-c0277d31f3da47c492e32103f7a79996

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05880270