Trifluoroacetic acid → (3,5-Dihydroxypicolinoyl)glycine

HRID 1798007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798007
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 (1 H, br s), 9.00 (1 H, t, J=6.1 Hz), 7.77 (1 H, d, J=2.4 Hz), 6.69 (1 H, d, J=2.4 Hz), 3.95 (1 H, d, J=6.2 Hz). HPLC-MS: m/z 213 [M+H]+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-049bd4e25baf4e8dbe8d5c743da7e2a2
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343952B2

Notizen zur Reaktion

Wird geladen…