Hydrochloric Acid → Methyl 4-(4'-amino-3'-fluoro-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

HRID 30870

Reaktionsgleichung

Reaktionsgleichung von HRID 30870
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:26])[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[NH:8]C=O.Cl>CO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:12]=[CH:13][C:14]([C:17](=[O:26])[CH2:18][C:19]([CH3:24])([CH3:25])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:16]=2)=[CH:3][C:2]=1[F:1]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 21985807Methyl 4-[3'-fluoro-4'-(formylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

Produkt 1

HCID 21985864Methyl 4-(4'-amino-3'-fluoro-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoateAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-[3′-fluoro-4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (1.21 g, 3.39 mmol) in methanol (10 mL) was added conc. HCl (3.5 mL), and the resulting solution was stirred at rt for 16 h. The mixture was then concentrated, diluted with water, and the acidity was adjusted to pH ˜7 by slow addition of saturated aqueous sodium bicarbonate solution. The mixture was then extracted with dichloromethane, and the combined organic layers were washed with saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was then triturated with ethyl acetate/hexane to afford methyl 4-(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (998 mg, 89%). LC-MS ret. time 3.11 min, m/z 329.9 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.31 (s, 6H), 3.28 (s, 2H), 3.66 (s, 3H), 6.84 (t, 1H), 7.21-7.35 (m, 2H), 7.55 (d, 2H), 7.93 (d, 2H).

Aufarbeitung

  1. concentrationThe mixture was then concentrated
  2. additiondiluted with water
  3. additionthe acidity was adjusted to pH ˜7 by slow addition of saturated aqueous sodium bicarbonate solution
  4. extractionThe mixture was then extracted with dichloromethane
  5. washthe combined organic layers were washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was then triturated with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-60e9608537f748319dc29b91b9c3c30d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423156B2

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