Reacción #1605799

ord-2a40e6429aeb40aa9905f622e7ded49f

Ecuación de reacción

[N-]=[N+]=NC[C@H](O)c1ccc(OCc2ccccc2)c2[nH]c(=O)ccc12
5-((R)-2-Azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one
CC(=O)O
acetic acid
CC(=O)O.NC[C@H](O)c1ccc(O)c2[nH]c(=O)ccc12
5-((R)-2-amino-1-hyroxyethyl)-8-hydroxy-1H-quinolin-2-one acetate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe catalyst was removed by filtration
  2. 2
    Concentraciónthe filtrate was concentrated under reduced pressure
  3. 3
    workup.ADDITIONTo the residue were added methanol (100 mL) and ethyl acetate (100 mL)
  4. 4
    workup.STIRRINGthe mixture was stirred
  5. 5
    FiltraciónThe precipitate was collected by filtration
  6. 6
    Otrodried

Procedimiento

5-((R)-2-Azido-1-hyroxyethyl)-8-benzyloxy-1H-quinolin-2-one (16.8 g, 49.9 mol) was suspended in acetic acid (50 mL), a catalytic amount of palladium hydroxide-carbon was added thereto, and the solution was stirred under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. To the residue were added methanol (100 mL) and ethyl acetate (100 mL), and the mixture was stirred. The precipitate was collected by filtration and dried to obtain 5-((R)-2-amino-1-hyroxyethyl)-8-hydroxy-1H-quinolin-2-one acetate (12.5 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09072734B2uspto-grants-2015_07