Sulfuric Acid → 5-[[(2,2-Dimethyl-1-oxopropyl)amino]methyl]-2-methylbenzoic acid

HRID 889534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889534
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].O[CH2:17][NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>O>[CH3:21][C:20]([CH3:23])([CH3:22])[C:19]([NH:18][CH2:17][C:13]1[CH:14]=[CH:15][C:7]([CH3:6])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])=[O:24]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 83732-Methylbenzoic acidHCID 13595971HCID 13595971, Verbindung

Produkt 1

HCID 679706855-[[(2,2-Dimethyl-1-oxopropyl)amino]methyl]-2-methylbenzoic acidAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Cool sulfuric acid (3.67 mL) to 0° C., and add 2-methylbenzoic acid (500 mg, 3.67 mmol, 1.0 equiv) and N-(hydroxymethyl)-2,2-dimethylpropanamide (506 mg, 3.86 mmol, 1.05 equiv). Allow the mixture to warm to room temperature, and stir overnight. Dilute with water (25 mL) and extract with EtOAc (50 mL). Dry the organic layer over MgSO4, filter, and concentrate under reduced pressure to give the crude compound. Purify the material by reverse-phase HPLC on an XBridge Prep C18 5 μM OBD 30×75 mm column, eluting with a gradient of 5-50% (0.1% TFA in acetonitrile) in (0.1% TFA in water) to give the title compound (255 mg, 28%). 1H NMR (DMSO-d6, 400 MHz): δ 12.76 (s, 1H), 8.09 (t, 1H, J=6.0 Hz), 7.67 (d, 1H, J=1.6 Hz), 7.25 (dd, 1H, J=8.0, 1.6 Hz), 7.21 (d, 1H, J=8.0 Hz), 4.22 (d, 2H, J=6.0 Hz), 2.46 (s, 3H), 1.10 (s, 9H).

Aufarbeitung

  1. extractionextract with EtOAc (50 mL)
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customto give the crude compound
  6. customPurify the material by reverse-phase HPLC on an XBridge Prep
  7. wash5 μM OBD 30×75 mm column, eluting with a gradient of 5-50% (0.1% TFA in acetonitrile) in (0.1% TFA in water)

Quellen und Nachweise

ORD-Eintrag
ord-ca07aaf999ef4044a7ef742d7e351023
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252831B2

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