Hydrochloric Acid → 2(R)-[3,3,3,2,2-pentafluoro-1(S)-(4-fluorophenyl)propylamino]-propionamide

HRID 1367822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367822
S[CH2:2][C@H:3]([NH:7][C@@H:8]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[C:4](O)=[O:5].[OH-].[Na+].ClCC1C=CC=C[N:28]=1.Cl>>[F:11][C:10]([F:13])([F:12])[C:9]([F:15])([F:14])[C@@H:8]([NH:7][C@H:3]([CH3:2])[C:4]([NH2:28])=[O:5])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 23393Picolyl chlorideHCID 866248312(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-3-mercaptopropionic acid

Produkt 1

HCID 866248332(R)-[3,3,3,2,2-pentafluoro-1(S)-(4-fluorophenyl)propylamino]-propionamide

Versuchsvorschrift

To a 0.2 M stock solution of 3-mercapto-2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-propionic acid in NaOH (10 mL, 2 mmol), 2-chloromethylpyridine (0.328 g, 2 mmol) and 1 N solution of NaOH (1 mL) were added. After stirring the reaction mixture for 5 h at room temperature, 1 M HCl solution was added until pH 5-6. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried over sodium sulfate and concentrated to give N-(1-cyanocyclopropyl)-3-pyridin-2-ylmethanesulfanyl)-2(R)-[3,3,3,2,2-pentafluoro-1(S)-(4-fluorophenyl)propylamino]-propionamide as a foam (0.692 g) which was converted to the title compound as described in Example 6 above.

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-012577685de64488aaa9175962e8712d
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893093B2

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