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Ethyl bromoacetate → HCID 18442482, Verbindung

HRID 458945
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 458945
[O:1]=[S:2]1(=[O:26])[C:8]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:7]=2[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][C:4]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:20][CH3:21])[CH2:3]1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>[O:26]=[S:2]1(=[O:1])[C:8]2[CH:9]=[C:10]([O:13][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:11]=[CH:12][C:7]=2[N:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][C:4]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:20][CH3:21])[CH2:3]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 9864334HCID 9864334, Verbindung

Produkt 1

HCID 18442482HCID 18442482, VerbindungAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysator
HCID 6342
Acetonitrile
Lösungsmittel

Versuchsvorschrift

1,1-Dioxo-3-butyl-3-ethyl-5-phenyl-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepin (WO9616051; 0.40 g, 1.07 mmol), ethyl bromoacetate (0.23 g, 1.38 mmol), sodium carbonate (0.50 g, 4.7 mmol) and tetrabutylammonium bromide (30 mg, 0.093 mmol) were added to MeCN (10 ml). The mixture was refluxed for 18 hours and then evaporated under reduced pressure. The residue was extracted with DCM/water. The DCM layer was separated and evaporated under reduced pressure. The residue was purified by column chromatography. The product was eluted with DCM/EtOAc (90:10). 0.480 g (97%) of the title compound was obtained. NMR (300 MHz) 0.7–0.85 (m, 6H), 1.0–1.7 (m, 11H), 3.1–3.3 (m, 2H), 3.6–3.8 (m, 2H), 4.3 (q, 2H), 4.6 (s, 2H), 6.9–7.3 (m, 7H), 7.5 (d, 1H).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 18 hours
  2. customevaporated under reduced pressure
  3. extractionThe residue was extracted with DCM/water
  4. customThe DCM layer was separated
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography
  7. washThe product was eluted with DCM/EtOAc (90:10)

Quellen und Nachweise

ORD-Eintrag
ord-b41942572ad64d8f8405bcc59ddc7023
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07192945B2

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