Ammonium Chloride → HCID 53694063, Verbindung

HRID 1600844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600844
[NH:1]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@H:2]([C:6]([NH:8][C@H:9]([CH:17]=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].Cl[C:30]([F:42])([F:41])[C:31](=[O:40])[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Cl-].[NH4+]>C1COCC1.[Ti](Cl)(Cl)(Cl)Cl.[Zn]>[CH2:22]([O:21][C:19]([NH:1][C@H:2]([C:6]([NH:8][CH:9]([CH:17]([OH:18])[C:30]([F:41])([F:42])[C:31](=[O:40])[CH2:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 72430Mdl-28170HCID 11042220145299-85-0

Produkt 1

HCID 53694063HCID 53694063, VerbindungAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 24193Titanium TetrachlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Add titanium tetrachloride (0.019 g, 0.1 eq) to a suspension of activated zinc (0.196 g, 3mAtg) in anhydrous THF (3 mL) at 0° C. under nitrogen. Stir 30 minutes and add CBz(L)-Val-Phe-H (0.42 g, 1.1 mmol), 1-chloro-1,1-difluoro-2-oxo-4-phenylbutane (0.218 g, 1.1 mmol), in anhydrous THF (4 mL). Allow the reaction to warm to room temperature and stir for 12 hours. Add a saturated solution of ammonium chloride (2 mL). Extract two times with diethyl ether (4 mL) and wash the organic phase with brine and dry over anhydrous magnesium sulphate. Concentrate the organic phase under vacuum. Purify the crude residue by flash chromatography (silica gel, 3:7 ethyl acetate:cyclohexane) to provide the title alcohol (0.381 g).

Aufarbeitung

  1. customthe reaction
  2. stirringstir for 12 hours
  3. extractionExtract two times with diethyl ether (4 mL)
  4. washwash the organic phase with brine
  5. dry with materialdry over anhydrous magnesium sulphate
  6. concentrationConcentrate the organic phase under vacuum
  7. customPurify the crude residue by flash chromatography (silica gel, 3:7 ethyl acetate:cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-82ba2768939e4a5ca3b6647503d9e0f7
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977074

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