Hydrochloric Acid → delta-Amino-N-butyl-gamma-hydroxy-alpha-methyl-cyclohexanehexanamide

HRID 1941351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941351
[CH2:1]([NH:5][C:6](=[O:28])[CH:7]([CH3:27])[CH2:8][CH:9]([OH:26])[CH:10]([NH:18]C(=O)[O:20]C(C)(C)C)[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4].Cl.[NH4+].[OH-]>O1CCOCC1>[NH4+:5].[OH-:20].[NH2:18][CH:10]([CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[CH:9]([OH:26])[CH2:8][CH:7]([CH3:27])[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:28]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 53864751[5-(Butylamino)-1-(cyclohexylmethyl)-2-hydroxy-4-methyl-5-oxopentyl]carbamic acid, 1,1-dimethylethyl ester

Produkt 2

HCID 14923Ammonium HydroxideHCID 19908509delta-Amino-N-butyl-gamma-hydroxy-alpha-methyl-cyclohexanehexanamideAusbeute 231,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of the product from A [1S-(1R*,2R*, 4R*)][5-(butylamino)-1-(cyclohexylmethyl)-2-hydroxy-4-methyl-5-oxopentyl]carbamic acid, 1,1-dimethylethyl ester (0.23 g, 0.58 mmol) in dioxane (5 mL) at 0° C. was added a dioxane solution (15 mL) saturated with HCl(g) and allowed to stand two h and then warm to r.t. for 16 h. The reaction was made basic (pH=8) by the dropwise addition of conc. NH4OH and then extracted with CH2Cl2. The organic layer was washed with water, dried (Na2CO3), filtered and concentrated in vacuo. Silica gel chromatography (90:10:1 CH2Cl2 :MeOH:NH4OH) of the concentrate afforded the title compound (0.20 g, 98%).

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a2225f5102c4252b6a5f98a69cb39fa
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703129

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