tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate → HCID 178453870, Verbindung

HRID 881689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881689
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][NH:14][C:13](=S)[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1.[NH2:25][CH2:26][CH:27]([C:29]1([C:32]([F:35])([F:34])[F:33])[CH2:31][CH2:30]1)[OH:28]>C(O)C.[Hg](Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:15][NH:14]/[C:13](=[N:25]\[CH2:26][CH:27]([OH:28])[C:29]2([C:32]([F:34])([F:35])[F:33])[CH2:31][CH2:30]2)/[C@H:12]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1

Komponenten

5

Edukt 2

HCID 59734935tert-Butyl (3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-ylcarbamate2×HCID 675258482-Amino-1-[1-(trifluoromethyl)cyclopropyl]ethanol

Produkt 1

HCID 178453870HCID 178453870, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24085Mercuric ChlorideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Mercury(II) chloride (149 mg, 0.547 mmol) was added to a solution of tert-butyl [(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]carbamate (150 mg, 0.421 mmol, described in Intermediate 7), and 2-amino-1-[1-(trifluoromethyl)cyclopropyl]ethanol (569 mg, 3.367 mmol) in ethanol (5 mL) at 60° C. After 10 min, the reaction was allowed to cool to ambient temperature. The mixture was filtered and concentrated under reduced pressure. Saturated aqueous NaHCO3 was added and the mixture was extracted with CH2Cl2 (3×). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=492 (M+1).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionSaturated aqueous NaHCO3 was added
  4. extractionthe mixture was extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-68740388d3404200bdf3059f9846546c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993588B2

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