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Triphenylphosphine → HCID 86661405, Verbindung

HRID 1908960
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1908960
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([CH2:51]O)[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35].S([O-])([O-])(=O)=O.[Mg+2]>O.C(OCC)(=O)C.O1CCCC1>[C:47]([O:46][C:44](=[O:45])[CH2:43][CH:42]1[CH2:51][N@@:41]1[C:39]([O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:40])([CH3:48])([CH3:49])[CH3:50]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5363146Diisopropyl azodicarboxylateHCID 11616071(S)-tert-Butyl 3-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Produkt 1

HCID 86661405HCID 86661405, VerbindungAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2.90 g of triphenylphosphine and 15 mL of tetrahydrofuran were added to 100 mL flask and the resulting reaction solution was cooled to 0° C. 2.17 mL of diisopropylazodicarboxylate was dropped while the reaction solution was stirred. After 30 minutes, 10 mL of tetrahydrofuran solution with 1.52 g of (S)-t-butyl 3-(t-butoxycarbonylamino)-4-hydroxybutanoate was dropped and stirred for 16 hours while the reaction temperature was naturally increased to room temperature. After completing the reaction, 40 mL of ethyl acetate and 40 mL of water were added to the reaction solution and then stirred for 10 minutes. An organic layer was isolated, dehydrated with magnesium sulfate, and then concentrated under reduced pressure. A concentrated residue was isolated with column chromatography (n-hexane:ethyl acetate=15:1) and then concentrated under reduced pressure to obtain 1.04 g of a title compound.

Aufarbeitung

  1. customthe resulting reaction solution
  2. stirringstirred for 16 hours while the reaction temperature
  3. temperaturewas naturally increased to room temperature
  4. additionwere added to the reaction solution
  5. stirringstirred for 10 minutes
  6. customAn organic layer was isolated
  7. concentrationconcentrated under reduced pressure
  8. customA concentrated residue was isolated with column chromatography (n-hexane:ethyl acetate=15:1)
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c67559a558e540b7b72ed3374ccc11f6
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598347B2

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