Water → 2,2-Dimethyl-propionic acid 8-ethoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester

HRID 1962366

Reaktionsgleichung

Reaktionsgleichung von HRID 1962366
[CH2:1]([O:3][N:4]1[CH2:24][CH2:23][C:7]2([NH:11][C:10](=[O:12])[C:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:8]2[OH:22])[CH2:6][CH2:5]1)[CH3:2].N1C=CC=CC=1.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].O>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][N:4]1[CH2:5][CH2:6][C:7]2([NH:11][C:10](=[O:12])[C:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:8]2[O:22][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:23][CH2:24]1)[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 596145818-Ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

Produkt 1

HCID 580312652,2-Dimethyl-propionic acid 8-ethoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 143 mg of 8-ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one in 1 ml of tetrahydrofuran were added 36 μl of pyridine and 53 μl of pivaloyl chloride. After stirring at room temperature for 20 hours, water and ethyl acetate were added and the phases separated. The aqueous phase was extracted with ethyl acetate, the combined organic phases dried with sodium sulfate, filtered and concentrated. Chromatography (heptane/ethyl acetate 2:1) yielded 117 mg of 2,2-dimethyl-propionic acid 8-ethoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester (title compound A54) as a solid, mp: 230-231° C.

Aufarbeitung

  1. customthe phases separated
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e070a7aaa4b7451a82b4176890038241
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415369B2

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