Triethylamine → Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoate

HRID 1469709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469709
[NH2:1][CH2:2][C:3]1[C:4]([F:15])=[C:5]([C:11]([Cl:14])=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].CCN(CC)CC.[C:23](Cl)(=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25]>C1COCC1.CCOC(C)=O>[Cl:14][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:15])[C:3]([CH2:2][NH:1][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 58483233Ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate

Produkt 1

HCID 58483442Ethyl 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoateAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-(aminomethyl)-6-chloro-2-fluorobenzoate (70 mg, 0.3 mmol) in THF (3 mL) were added Et3N (0.105 mL, 0.76 mmol) and pivaloyl chloride (38 μL, 0.31 mmol). The reaction mass was stirred at rt for 2 h, diluted with EtOAc and was washed with water, and brine. The organic layer was separated, dried, filtered and concentrated to afford 70 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.15 (br t, 1H), 7.43-7.35 (m, 2H), 4.38 (q, J=7.2 Hz, 2H), 4.26 (d, J=5.7 Hz, 2H), 1.30 (t, J=6.9 Hz, 3H), 1.11 (s, 9H).

Aufarbeitung

  1. washwas washed with water, and brine
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-83ffd3354fad4a3a8255618d57d452b5
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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