Triethylamine → HCID 57974061, Verbindung

HRID 1615819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615819
C([S@@]([NH:7][C@H:8]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)[CH2:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12](OC)=[O:13])=O)(C)(C)C.C(N(CC)CC)C>CO>[F:25][C:20]1[CH:19]=[C:18]([C@H:8]2[NH:7][C:12](=[O:13])[C:11]([CH3:17])([CH3:16])[CH2:10][CH2:9]2)[CH:23]=[C:22]([F:24])[CH:21]=1

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 66864959Methyl (δS)-δ-[[(S)-(1,1-dimethylethyl)sulfinyl]amino]-3,5-difluoro-α,α-dimethylbenzenepentanoate

Produkt 1

HCID 57974061HCID 57974061, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of methyl (5S)-5-{[(S)-tert-butylsulfinyl]amino}-5-(3,5-difluorophenyl)-2,2-dimethylpentanoate from Step E (300 mg, 0.800 mmol) in MeOH (16 mL) was cooled to 0° C. Hydrogen chloride gas (anhydrous) was bubbled through this cold solution for about 30 seconds, after which time the reaction vessel was sealed and allowed to sit in the ice bath for 15 minutes. Dry nitrogen was then bubbled through the solution for 30 minutes, prior to removal of solvent in vacuo. More MeOH (˜50 mL) was added, and then removed in vacuo. After dissolving in a third volume of MeOH (16 mL), triethylamine (323 mg, 3.2 mmol) was introduced and the mixture was heated to 65° C. for 16 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was partitioned between diethyl ether (50 mL) and 1 N HCl (50 mL). The organics were washed with additional 1 N HCl (50 mL), water (50 mL) and saturated brine (50 mL). The ethereal solution was dried over sodium sulfate, filtered and then concentrated in vacuo to provide the title compound, which could be used without further purification. MS: m/z=240 (M+1).

Aufarbeitung

  1. customHydrogen chloride gas (anhydrous) was bubbled through this cold solution for about 30 seconds
  2. customafter which time the reaction vessel was sealed
  3. customDry nitrogen was then bubbled through the solution for 30 minutes
  4. customto removal of solvent in vacuo
  5. additionMore MeOH (˜50 mL) was added
  6. customremoved in vacuo
  7. additionwas introduced
  8. temperatureAfter cooling to ambient temperature
  9. customthe solvent was removed in vacuo
  10. customthe residue was partitioned between diethyl ether (50 mL) and 1 N HCl (50 mL)
  11. washThe organics were washed with additional 1 N HCl (50 mL), water (50 mL) and saturated brine (50 mL)
  12. dry with materialThe ethereal solution was dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e47cf65b5b294756a66132daedfbad93
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765759B2

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