1,4-Dioxane → t-Butyl 3-[[5-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]propionate

HRID 2080447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080447
Cl.[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])([CH3:5])([CH3:4])[CH3:3].O1CCOCC1.Cl[C:19]1[CH:24]=[C:23]([CH:25]([S:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:22]([Cl:42])=[CH:21][N:20]=1>C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>[Cl:42][C:22]1[C:23]([CH:25]([S:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])=[CH:24][C:19]([NH:10][CH2:9][CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])=[N:20][CH:21]=1

Komponenten

6

Edukt 3

HCID 312751,4-DioxaneHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 231145672,5-Dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine

Produkt 1

HCID 23114708t-Butyl 3-[[5-chloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]propionateAusbeute 20,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

In a small amount of a saturated aqueous solution of potassium carbonate was dissolved β-alanine t-butyl ester hydrochloride (1.5 g), followed by extraction with methylene chloride. The extract was dried and concentrated into 720 mg of β-alanine t-butyl ester in the free form. The resulting ester and a 1,4-dioxane (2.0 ml) solution of the 2,5-dichloro-4-[(4-chlorophenylthio)-(2,5-difluorophenyl)methyl]pyridine (300 mg, 0.72 mmol) obtained in Example 54 was stirred at 120° C. for 4 days under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate. The diluted mixture was washed with water and brine, dried and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (79 mg, 16%) as an oil.

Aufarbeitung

  1. extractionfollowed by extraction with methylene chloride
  2. customThe extract was dried
  3. concentrationconcentrated into 720 mg of β-alanine t-butyl ester in the free form
  4. washThe diluted mixture was washed with water and brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-2d2d59f7a84b4546903d80a791ddec2c
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932271B2

Notizen zur Reaktion

Wird geladen…