Ammonium Chloride → HCID 68907678, Verbindung

HRID 546482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546482
C[Li].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][C@H:15](C(OCC)=O)[CH2:14][CH2:13][C@H:12]1[NH:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=2)=[O:24])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>O1CCCC1>[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][C@H:15]([C:3]([OH:7])([CH3:5])[CH3:4])[CH2:14][CH2:13][C@H:12]1[NH:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=2)=[O:24])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 67056493HCID 67056493, VerbindungHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 68907678HCID 68907678, VerbindungAusbeute 118,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyllithium (1.14N solution, 2.27 ml) was added to a tetrahydrofuran solution (10 ml) of (1R*,2S*,4R*)-N2-tert-butoxycarbonyl-N1-[(5-chloroindol-2-yl)carbonyl]-4-ethoxycarbonyl-1,2-cyclohexanediamine (200 mg) at −78° C., and the mixture was stirred for 1 hour and then 2 hours under ice cooling. An aqueous solution of ammonium chloride was added to the reaction mixture to extract the reaction mixture with chloroform, and the resultant organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3) to obtain the title compound (115 mg) as a colorless solid.

Aufarbeitung

  1. custom2 hours
  2. extractionto extract the reaction mixture with chloroform
  3. washthe resultant organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-291db93d7f374011b2ab71f0d64a50f9
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935824B2

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