tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate → HCID 58802705, Verbindung

HRID 14084

Reaktionsgleichung

Reaktionsgleichung von HRID 14084
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[CH:23]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30])([CH3:25])[CH3:24]>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]([OH:12])[CH2:13][NH:30][CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[C:26]([CH:23]([CH3:25])[CH3:24])[CH:27]=1

Komponenten

4

Edukt 2

HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 210858343-Isopropylbenzylamine Hydrochloride

Produkt 1

HCID 58802705HCID 58802705, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate (2.0 g, 6.7 mmol) and 3-isopropylbenzylamine hydrochloride (2.5 g, 13.5 mmol) in isopropanol (60 mL) are refluxed 3 h. The reaction is cooled and stirred 16 h. The solution is concentrated under reduced pressure, redissolved in chloroform, washed with 1N hydrochloric acid, saturated sodium bicarbonate, brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash chromatography (silica, 7% methanol/chloroform) gives the title compound in pure form. ESI MS m/z 449.3 [M+H]+.

Aufarbeitung

  1. temperatureThe reaction is cooled
  2. concentrationThe solution is concentrated under reduced pressure
  3. dissolutionredissolved in chloroform
  4. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate, brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (silica, 7% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-548e25f629284c9bb15e616e70c4019b
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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