Water → 1-((Tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid

HRID 352201

Reaktionsgleichung

Reaktionsgleichung von HRID 352201
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+]>O1CCCC1.CN(C1C=CN=CC=1)C>[C:2]([O:13][C:12]([NH:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:15])([CH3:8])([CH3:7])[CH3:3]

Komponenten

6

Edukt 3

HCID 962WaterHCID 13661-Aminocyclohexanecarboxylic acidHCID 11430Potassium Carbonate

Produkt 1

HCID 27947441-((Tert-butoxycarbonyl)amino)cyclohexanecarboxylic acidAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a slurry of 1-amino-1-cyclohexane-carboxylic acid, 5.0 g (35.0 mmol) in 50 mL of tetrahydrofuran and 50 mL of water was added 14.5 g (105.0 mmol) of potassium carbonate, 7.7 g (35.0 mmol) of BOC-anhydride and 5 mg of DMAP. The mixture was stirred overnight at rt. and the organics were evaporated off in vacuo. The aqueous layer was acidified to pH=1 with 5 N HCl and extracted with 20% isopropanol/chloroform. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to dryness to yield 1.83 g (21%) of the desired product as a white oil that solidifies upon standing. MS (IS) 244.2 (M+).

Aufarbeitung

  1. customand the organics were evaporated off in vacuo
  2. extractionextracted with 20% isopropanol/chloroform
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-dc81a18f009e4f41ae31c62b05384ab5
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743794B2

Verknüpfte Notizen

Wird geladen…