Trifluoroacetic acid → (3,5-Dihydroxypicolinoyl)glycine

HRID 1430201Notes

Reaction equation

HRID 1430201 reaction equation
C([O:5][C:6](=[O:19])[CH2:7][NH:8][C:9]([C:11]1[C:16]([OH:17])=[CH:15][C:14]([OH:18])=[CH:13][N:12]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:17][C:16]1[C:11]([C:9]([NH:8][CH2:7][C:6]([OH:19])=[O:5])=[O:10])=[N:12][CH:13]=[C:14]([OH:18])[CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59513079[(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-acetic acid tert-butyl ester

Product 1

HCID 24891198(3,5-Dihydroxypicolinoyl)glycineYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe solid that remains is collected by filtration
  3. washwashed with Et2O

Sources & evidence

ORD record
ord-e85d2d2736764515baa5e022490fc626
Source dataset
uspto-grants-2015_01
Patent number
US08940773B2

Reaction notes

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