(Diethylamino)sulfur trifluoride → HCID 86692272, Verbindung

HRID 1469798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469798
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18]O)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:29])CC)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18][F:29])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86692262HCID 86692262, Verbindung

Produkt 1

HCID 86692272HCID 86692272, VerbindungAusbeute 51,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 6-chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzoate (Intermediate-59, step 1, 200 mg, 0.60 mmol) in THF (2 mL) was added diethylaminosulfur trifluoride (146 mg, 0.90 mmol) and the reaction mixture was stirred at rt for 12 h. Then the reaction mixture was quenched with water and was extracted with CHCl3. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 0.104 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.32 (t, 1H), 7.44-7.36 (m, 2H), 4.47-4.29 (m, 6H), 1.33-1.29 (t, J=6.9 Hz, 3H), 1.14 (s, 6H).

Aufarbeitung

  1. customThen the reaction mixture was quenched with water
  2. extractionwas extracted with CHCl3
  3. washThe organic layer was washed with brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-60c4ae4065d7497d9cfb4880775125e3
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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