Cyclooctanone → HCID 20794995, Verbindung

HRID 1070566

Reaktionsgleichung

Reaktionsgleichung von HRID 1070566
[C:1]([CH:5]([C:12]([OH:14])=[O:13])[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:15]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.C(O)(=O)C>[CH:15]1([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:12]([OH:14])=[O:13])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 10403CyclooctanoneHCID 5049666Sodium triacetoxyborohydrideHCID 18611299HCID 18611299, Verbindung

Produkt 1

HCID 20794995HCID 20794995, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21926011acetic acid N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of γ-tert-butyl-L-glutamic acid (4.06 g, 20.0 mmol) and cyclooctanone (3.15 g, 25 mmol) in N,N-dimethylformamide/acetic acid (99:1, v/v, 50 mL) was added sodium triacetoxyborohydride (6.36 g, 30.0 mmol) in small portions and the mixture was stirred overnight. After evaporation of the solvent, the residue was dissolved in water (50 mL). The pH was adjusted to 9 with 2 N sodium hydroxide solution, followed by extraction with diethylether (50 mL). Subsequently, the pH of the aqueous layer was carefully adjusted to 2.5 using 1.0 N hydrochloric acid. Extraction with dichloromethane afforded an organic layer, which was dried (magnesium sulphate) and concentrated under reduced pressure, yielding 4.82 g (77%) of the title compound as a white solid. ESI-MS: 314.2 (M+H)+, 336.2 (M+Na)+. Rf (silica gel; ethyl acetate/pyridine/acetic acid/water 63:20:6:11, v/v): 0.80.

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in water (50 mL)
  3. extractionfollowed by extraction with diethylether (50 mL)
  4. extractionExtraction with dichloromethane
  5. customafforded an organic layer, which
  6. dry with materialwas dried (magnesium sulphate)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e2a1594e01674934b1831cd8b4d0e173
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06903107B1

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