Sodium Iodide → HCID 18931124, Verbindung

HRID 1599002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1599002
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:3]1.Br[CH2:21][CH:22]([OH:25])[CH2:23][OH:24].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH2:21][CH:22]([OH:25])[CH2:23][OH:24])[C:5](=[O:7])[C:4]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[NH:3]1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 208273-Bromo-1,2-propanediol2×HCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Produkt 1

HCID 18931124HCID 18931124, VerbindungAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of tert-butyl 2,4-dioxo-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (6.9 g, 25.6 mmol), 3-bromo-1,2-propanediol (4.4 g, 28 mmol), sodium iodide (1.5 g, 10 mmol), potassium carbonate (14 g) and DMF (25 mL) was stirred approximately 48 hours at 100° C. Additional 3-bromo-1,2-propanediol (1.5 g, 10 mmol) was added, and the stirring and heating continued for an additional 72 hours. After cooling, the mixture was filtered, the solvent removed from the filtrate under vacuum, and the residue was purified by chromatography eluting with ethyl acetate containing 0.5-1% acetic acid. The fractions containing the product were combined and concentrated, and the residue was treated with ethyl acetate to give tert-butyl 2,4-dioxo-3-(2,3-dihydroxypropyl)-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (1.5 g, 4.4 mmol) as a white solid, m.p. 167°-170° C.

Aufarbeitung

  1. temperaturethe stirring and heating
  2. waitcontinued for an additional 72 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe solvent removed from the filtrate under vacuum
  6. customthe residue was purified by chromatography
  7. washeluting with ethyl acetate containing 0.5-1% acetic acid
  8. additionThe fractions containing the product
  9. concentrationconcentrated
  10. additionthe residue was treated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b16ae4bca1d4472196a882a508e07e35
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739336

Notizen zur Reaktion

Wird geladen…