Hydrochloric Acid → HCID 22467131, Verbindung

HRID 1934737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934737
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][CH:14]([CH3:33])[CH2:15][CH:16]=[C:17]1[CH2:32][CH2:31][C:20]2([S:24][CH2:23][C:22](=[O:25])[N:21]2[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:19][CH2:18]1.Br[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].Cl>CCCCCC.O1CCCC1.C(OCC)(=O)C>[C:39]([O:38][C:36](=[O:37])[CH2:35][CH:23]1[C:22](=[O:25])[N:21]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:20]2([CH2:31][CH2:32][C:17](=[CH:16][CH2:15][CH:14]([CH3:33])[CH3:13])[CH2:18][CH2:19]2)[S:24]1)([CH3:42])([CH3:41])[CH3:40]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 79177tert-Butyl bromoacetateHCID 224671633-[8-(3-Methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acidHCID 178418339Butyllithium

Produkt 1

HCID 22467131HCID 22467131, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

In an atmosphere of nitrogen, 1.97 ml of N,N-diisopropylamine was added to 10 ml of anhydrous tetrahydrofuran, to which was dropwise added 9.50 ml of a solution of n-butyllithium in hexane (1.58 mol/L) at −30° C. The mixture was stirred at the same temperature for 10 minutes and then cooled to −70° C., to which was dropwise added a solution of 1.56 g of 3-[8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid in 20 ml of anhydrous tetrahydrofuran. After stirring the resulting mixture at the same temperature as above for 30 minutes, 0.89 ml of tert-butyl bromoacetate was dropwise added at the same temperature. After elevating the temperature to 0° C., the reaction mixture was poured into a mixture of ice water and ethyl acetate, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus, 2.23 g of 3-[2-[2-(tert-butoxy)-2-oxoethyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid was obtained as a yellow oily product.

Aufarbeitung

  1. customat −30° C
  2. additionwas dropwise added at the same temperature
  3. customto 0° C.
  4. customthe organic layer was separated
  5. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a543183556fc4db58b35f61a7a5b9e79
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384065B1

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