Benzyl 6-oxopyran-3-carboxylate → Benzyl 1-(2-(tert-butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 509410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509410
O=[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4][O:3]1.Cl.[C:19]([O:23][C:24](=[O:27])[CH2:25][NH2:26])([CH3:22])([CH3:21])[CH3:20]>CO>[C:19]([O:23][C:24](=[O:27])[CH2:25][N:26]1[C:2](=[O:3])[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4]1)([CH3:22])([CH3:21])[CH3:20]

Komponenten

4

Edukt 2

HCID 325763Benzyl 6-oxopyran-3-carboxylateHCID 2725036Glycine tert-butyl ester hydrochloride

Produkt 1

HCID 86687994Benzyl 1-(2-(tert-butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A solution of benzyl 2-oxo-2H-pyran-5-carboxylate (906 mg, 3.94 mmol) and glycine tert butyl ester hydrochloride (726 mg, 4.33 mmol) in MeOH (20 mL) was treated with TEA (1.642 mL, 11.81 mmol). The reaction was stirred at 23° C. under nitrogen. After 1 h, the solution was concentrated in vacuo and purified by silica gel chromatography (eluent: 10-50% EtOAc/hexane), affording the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=2.35 Hz, 1H), 7.90 (dd, J=9.59, 2.54 Hz, 1H), 7.31-7.54 (m, 5H), 6.55 (d, J=9.59 Hz, 1H), 5.30 (s, 2H), 4.56 (s, 2H), 1.48 (s, 9H). MS (ESI, positive ion) m/z: 366.0 (M+H).

Aufarbeitung

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by silica gel chromatography (eluent: 10-50% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9827ccc80cb0404fb0e5ac857e89e8e7
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096527B2

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