N,N-Dimethylaniline → HCID 178429631, Verbindung

HRID 127653

Reaktionsgleichung

Reaktionsgleichung von HRID 127653
O(CC([NH:11][C@@H:12]1[C:23](=[O:24])[N:14]2[C:15]([C:20]([OH:22])=[S:21])=[C:16]([CH3:19])[CH2:17][S:18][C@H:13]12)=O)C1C=CC=CC=1.CN(C)C1C=CC=CC=1.C[Si](C)(Cl)Cl.P(Cl)(Cl)(Cl)(Cl)Cl>C(Cl)Cl.O.O1CCOCC1.C(O)CCC>[NH2:11][C@@H:12]1[C:23](=[O:24])[N:14]2[C:15]([C:20]([OH:22])=[S:21])=[C:16]([CH3:19])[CH2:17][S:18][C@H:13]12

Komponenten

9

Edukt 4

HCID 949N,N-Dimethylaniline2×HCID 6398DichlorodimethylsilaneHCID 24819Phosphorus pentachlorideHCID 178429632HCID 178429632, Verbindung

Produkt 1

HCID 178429631HCID 178429631, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A suspension of 3.80 g (10 mmols) of 7β-phenoxyacetamido-3-methylthio-ceph-3-em-4-carboxylic acid in 38 ml of absolute methylene chloride is stirred with 4.45 ml of dimethylaniline and 1.50 ml of dimethyldichlorosilane for 30 minutes at room temperature. The reaction mixture is cooled to -20° C., 2.60 g of phosphorus pentachloride are added, the mixture is stirred for 30 minutes at -20° C. and is then added dropwise to a mixture, cooled to -20° C., of 15.5 ml of n-butanol and 1.47 ml of dimethylaniline. The temperature is allowed to rise to -10° C. and 15.5 ml of dioxane and 0.53 ml of water are added. When crystallisation starts, the pH value is adjusted to 4.1 with tributylamine and crystallisation is brought to completion by stirring for 2 hours at 0°-5° C. The precipitate is filtered off, washed with 10 ml of dioxane and 5 ml of methylene chloride and dried in a high vacuum. 7β-Amino-3-methylthio-ceph-3-em-4-carboxylic acid of melting point 205° C. (decomposition) is obtained; UV spectrum (0.1 N NaHCO3): λmax =293 (ε=7600); IR spectrum (nujol): characteristic bands at 3.15, 5.55 6.17 and 6.53μ.

Aufarbeitung

  1. additionis then added dropwise to a mixture
  2. customto rise to -10° C.
  3. customWhen crystallisation
  4. customthe pH value is adjusted to 4.1 with tributylamine and crystallisation
  5. stirringby stirring for 2 hours at 0°-5° C
  6. filtrationThe precipitate is filtered off
  7. washwashed with 10 ml of dioxane and 5 ml of methylene chloride
  8. customdried in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fc782fc3eefe4c5ba419988ea529d6ea
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256739

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