Diisopropyl Ether → Benzhydryl 7-amino-3-allylthiomethyl-3-cephem-4-carboxylate

HRID 1494478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494478
P(Cl)(Cl)(Cl)(Cl)Cl.C1(CC([NH:16][CH:17]2[C:45](=[O:46])[N:19]3[C:20]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:21]([CH2:24][S:25][CH2:26][CH:27]=[CH2:28])[CH2:22][S:23][C@H:18]23)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+].C(OC(C)C)(C)C>C(Cl)Cl.O.CO.N1C=CC=CC=1>[NH2:16][CH:17]1[C:45](=[O:46])[N:19]2[C:20]([C:29]([O:31][CH:32]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:30])=[C:21]([CH2:24][S:25][CH2:26][CH:27]=[CH2:28])[CH2:22][S:23][C@H:18]12

Komponenten

9

Edukt 4

HCID 7914Diisopropyl EtherHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 67712927Benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate

Produkt 1

HCID 67712680Benzhydryl 7-amino-3-allylthiomethyl-3-cephem-4-carboxylateAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a suspension of phosphorus pentachloride (16.1 g) and pyridine (6.3 ml) in methylene chloride (100 ml) were added benzhydryl 7-(2-phenylacetamido)-3-allylthiomethyl-3-cephem-4-carboxylate (22 g) and methylene chloride (100 ml) at 5° C., and the mixture was stirred at the same temperature for an hour. After cooling to -20° C., methanol (10 ml) was added thereto, followed by stirring at -10° C. for half an hour. To this mixture was added water (10 ml) and stirred for 10 minutes. To the separated methylene chloride was added an aqueous solution of sodium bicarbonate until the pH value of the aqueous solution became 5.0, and the mixture was shaken. After separating out the organic layer, it was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue obtained was pulverized with diisopropyl ether to give benzhydryl 7-amino-3-allylthiomethyl-3-cephem-4-carboxylate (6.5 g).

Aufarbeitung

  1. stirringby stirring at -10° C. for half an hour
  2. stirringstirred for 10 minutes
  3. stirringthe mixture was shaken
  4. customAfter separating out the organic layer, it
  5. washwas washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-c7594e68de0149a5b8e83e0d3ece5ffd
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05026695

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