Reaction #2275715

Reaction equation

[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

trifluoroacetic acid

→

desired compound

Yield 89.0%

[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid

Yield 89.0%

Solvents

CH2Cl2

Conditions

Workup

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

Procedure

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