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Triethyl phosphonoacetate → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate

HRID 1022672
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1022672
[Cl-].[Li+].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[CH2:25]([O:27][C:28](=[O:38])[CH2:29]P(OCC)(OCC)=O)[CH3:26].[Cl:39][C:40]1[CH:41]=[C:42]([C@@H:47]2[O:53][CH2:52][CH2:51][N:50]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:49][C@H:48]2[CH:61]=O)[CH:43]=[CH:44][C:45]=1[Cl:46]>C(#N)C>[Cl:39][C:40]1[CH:41]=[C:42]([C@@H:47]2[O:53][CH2:52][CH2:51][N:50]([C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:49][C@H:48]2/[CH:61]=[CH:29]/[C:28]([O:27][CH2:25][CH3:26])=[O:38])[CH:43]=[CH:44][C:45]=1[Cl:46]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 13345Triethyl phosphonoacetateHCID 433294Lithium ChlorideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 86663853tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate

Produkt 1

HCID 66976531tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-1,4-oxazepane-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of lithium chloride (136 mg) and diazabicycloundecene (0.403 mL) in acetonitrile (26.7 mL) was added ethyl(diethoxyphosphoryl)acetate (0.642 mL), and the mixture was stirred at 20 min. tert-Butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-formyl-1,4-oxazepane-4-carboxylate (1.00 g) was added and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (902 mg).

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with distilled water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1cadf7c38a29422cac3f4ee99ee9b35c
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722662B2

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