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Triethylamine → HCID 178468133, Verbindung

HRID 1763470
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1763470
[NH2:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[CH2:7][S:8][C@H:3]12.C(N(CC)CC)C.[F:35][C:36]([F:45])([F:44])[CH2:37][S:38]([CH2:40][C:41](O)=[O:42])=[O:39]>CN(C)C=O>[F:35][C:36]([F:45])([F:44])[CH2:37][S:38]([CH2:40][C:41]([NH:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[CH2:7][S:8][C@H:3]12)=[O:42])=[O:39]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 205740232-(2,2,2-Trifluoroethanesulfinyl)acetic acidHCID 178468132HCID 178468132, Verbindung

Produkt 1

HCID 178468133HCID 178468133, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 4.36 g (0.01 mol) of 7β-amino-3-(1-ethoxyhydroxyphosphinylmethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid in 50 ml of dry dimethylformamide is treated with 4 ml of triethylamine and the mixture is stirred for 15 minutes at 25°. A slight excess of 0.01 mol of the activated ester of 2,2,2-trifluoroethylsulfinylacetic acid is added to the mixture and it is stirred an additional hour. The reaction mixture is evaporated to dryness and water and ethyl acetate are added to the residue. The layers are separated, the ethyl acetate layer is discarded, fresh ethyl acetate is added to the aqueous phase and it is acidified to pH 2.5 by addition of 6N hydrochloric acid. The mixture is filtered, the layers are separated and the aqueous phase is treated with Amberlite IR-120H ion-exchange resin and lyophilized to give the title compound.

Aufarbeitung

  1. stirringis stirred an additional hour
  2. customThe reaction mixture is evaporated to dryness and water and ethyl acetate
  3. additionare added to the residue
  4. customThe layers are separated
  5. additionfresh ethyl acetate is added to the aqueous phase and it
  6. additionis acidified to pH 2.5 by addition of 6N hydrochloric acid
  7. filtrationThe mixture is filtered
  8. customthe layers are separated
  9. additionthe aqueous phase is treated with Amberlite IR-120H ion-exchange resin

Quellen und Nachweise

ORD-Eintrag
ord-7fd747cfdcdd4dd4a42dca24dfe73d0d
Quelldatensatz
uspto-grants-1978_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04112086

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