Acetic Acid → 6-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl ester

HRID 23228

Reaktionsgleichung

Reaktionsgleichung von HRID 23228
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=2[CH:15]=O)[CH:6]=1)=[O:4].[F:19][C:20]([F:31])([F:30])[O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.CC(O)=O.C([BH3-])#N.[Na+]>CCO>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=2[CH2:15][NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][C:20]([F:19])([F:30])[F:31])=[CH:23][CH:24]=2)[CH:6]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5718464-(Trifluoromethoxy)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 118068606-Methoxy-5-formyl-2-naphthoic acid methyl ester

Produkt 1

HCID 697331386-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl esterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 6-methoxy-5-formyl-2-naphthoic acid methyl ester (1.09 g, 4.46 mmol) in EtOH (40 mL) at room temperature was added 4-trifluoromethoxy-benzyl amine (0.749 mL, 4.91 mmol) followed by HOAc (0.255 mL, 4.46 mmol). After 10 min. at this temperature, sodium cyanoborohydride (0.420 g, 6.69 mmol) was added, and reaction was continued stirring at rt for 4 h. After 1 h at this temperature, the reaction was heated to 45° C. for 2 h. The solution was quenched with sat. aq. NaHCO3 (20 mL) and then extracted with EtOAc (200 mL). The organic layer was washed with brine (20 mL) and dried (MgSO4). After concentration, the residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient) to afford the product (0.780 g, 42%) as a solid; 1H NMR (DMSO-d6) δ3.77 (s, 2H), 3.86 (s, 3H), 3.88 (s, 3H), 4.07 (s, 2H), 7.26 (d, J =8.0 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.48 (d, J=9.2 Hz, 1H), 7.88 (dd, J=1.9, 8.9 Hz, 1H), 8.06 (d, J=5.2 Hz, 1H), 8.08 (d, J=5.3 Hz, 1H), 8.52 (d, J=1.7 Hz, 1H); mass spectrum [(+) El], m/z 420 (M+H)+.

Aufarbeitung

  1. customreaction
  2. waitAfter 1 h at this temperature
  3. temperaturethe reaction was heated to 45° C. for 2 h
  4. customThe solution was quenched with sat. aq. NaHCO3 (20 mL)
  5. extractionextracted with EtOAc (200 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationAfter concentration
  9. customthe residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5f4aae98621c43a4ab8358138b73fa10
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849761B2

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