2,6-Difluorobenzylamine → HCID 69615296, Verbindung

HRID 495528

Reaktionsgleichung

Reaktionsgleichung von HRID 495528
[CH3:1][C:2]1O[CH:4]=[CH:5][C:6](=[O:25])[C:7]=1[O:8][CH2:9][C@:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:28]=1[CH2:29][NH2:30]>C(O)C>[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:28]=1[CH2:29][N:30]1[CH:4]=[CH:5][C:6](=[O:25])[C:7]([O:8][CH2:9][C@:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([NH2:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]1[CH3:1]

Komponenten

4

Edukt 2

HCID 1235632,6-DifluorobenzylamineHCID 86588579HCID 86588579, Verbindung

Produkt 1

HCID 69615296HCID 69615296, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Crude 2-methyl-3-[(2R)-Boc-amino-2-phenylethoxy]-4H-pyran-4-one (1.00 g, ˜2.90 mmol), 2,6-difluorobenzyl amine (700 μL, 5.8 mmol) and ethanol (3 mL) were combined and heated to 120° C. in a pressure vessel. After 16 h, the volatiles were removed in vacuo and the residue purified by column chromatography, eluting with EtOAc. The product was isolated as a white foam (204 mg, 0.43 mmol, 15%, assuming pure starting material). 1H NMR (CDCl3-300 MHz) δ 7.42-7.19 (m, 7H); 6.98 (t, J=8.1 Hz, 2H); 6.43 (d, J=7.8 Hz, 1H); 5.06 (s, 2H); 4.87-4.83 (m, 1H); 4.06 (dd, J1=9.9 Hz, J2=4.2 Hz, 1H); 3.93 (dd, J=9.9 Hz, J2=6.8 Hz, 1H); 2.34 (s, 3H); 1.42 (s, 9H); LRMS m/z 471.1 (M++1), 371.0 (M+−boc+1).

Aufarbeitung

  1. customthe volatiles were removed in vacuo
  2. customthe residue purified by column chromatography
  3. washeluting with EtOAc
  4. customThe product was isolated as a white foam (204 mg, 0.43 mmol, 15%, assuming pure starting material)

Quellen und Nachweise

ORD-Eintrag
ord-cc9105308f0f48048ed1200097c98913
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939883B2

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