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Water → HCID 7019898, Verbindung

HRID 2399239
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2399239
[NH:1]1[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].C(N(CC)CC)C.O.[CH3:28][C:29]([O:32][C:33](ON=C(C1C=CC=CC=1)C#N)=[O:34])([CH3:31])[CH3:30]>CC(C)=O>[N:1]1([C:33]([O:32][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:34])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 6351946Pro-Phe

Produkt 1

HCID 7019898HCID 7019898, VerbindungAusbeute 144,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

To a solution of L-Pro-L-Phe (1.0 g, 3.8 mmol) and triethylamine (0,794 ml, 5.7 mmol) in 1:1 water:acetone (38 ml) was added Boc-ON (1.13 g, 4.6 mmol), and the reaction mixture stirred at room temperature for 9 hours. Acetone was removed by evaporation under reduced pressure and the resulting aqueous solution diluted with a solution of saturated sodium bicarbonate and then washed with ether. The remaining aqueous phase was acidified to pH 2.0 and extensively extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated to yield 1.99 g of N-Boc-L-Pro-L-Phe as a white glassy solid.

Aufarbeitung

  1. customAcetone was removed by evaporation under reduced pressure
  2. additionthe resulting aqueous solution diluted with a solution of saturated sodium bicarbonate
  3. washwashed with ether
  4. extractionextensively extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5f7d86fc86cc451694bc03833cc93d39
Quelldatensatz
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05447915

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