Reacción #2275715

ord-427d8ca9ad2f4817b5a404659a2e8806

Ecuación de reacción

CC(C)(C)OC(=O)CNC(=O)c1ncc(O)cc1O
[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
O=C(O)CNC(=O)c1ncc(O)cc1O
desired compound
Rendimiento 89.0%
O=C(O)CNC(=O)c1ncc(O)cc1O
[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid
Rendimiento 89.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated under reduced pressure
  2. 2
    FiltraciónThe solid that remains is collected by filtration
  3. 3
    Lavadowashed with Et2O

Procedimiento

To a solution of [(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester, 28, (0.10 g, 0.37 mmol) in CH2Cl2 (4 mL) at room temperature is added trifluoroacetic acid (1 mL). The reaction is stirred for 16 hours at room temperature and then concentrated under reduced pressure. The solid that remains is collected by filtration, washed with Et2O to afford 0.070 g (89% yield) of the desired compound as a colorless solid. 1H NMR (250 MHz, DMSO-d6) δ ppm 10.86 (1H, br s), 9.00 (1H, t, J=6.1 Hz), 7.77 (1H, d, J=2.4 Hz), 6.69 (1H, d, J=2.4 Hz), 3.95 (1H, d, J=6.2 Hz). HPLC-MS: m/z 213 [M+H]+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08323671B2uspto-grants-2012_12