Réaction #2275715

ord-427d8ca9ad2f4817b5a404659a2e8806

Équation de réaction

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
Rendement 89.0%
O=C(O)CNC(=O)c1ncc(O)cc1O
[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid
Rendement 89.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Concentrationconcentrated under reduced pressure
  2. 2
    FiltrationThe solid that remains is collected by filtration
  3. 3
    Lavagewashed with Et2O

Mode opératoire

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]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08323671B2uspto-grants-2012_12