StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

tert-Butanol → t-Butyl 7-benzamido-3-methyl-3-cephem-4-carboxylate 1-oxide

HRID 67954
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 67954
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17].[C:21]([NH:29][CH:30]1[C:42](=[O:43])[N:32]2[C:33]([C:39](O)=[O:40])=[C:34]([CH3:38])[CH2:35][S:36](=[O:37])[C@H:31]12)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[C:21]([NH:29][CH:30]1[C:42](=[O:43])[N:32]2[C:33]([C:39]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:40])=[C:34]([CH3:38])[CH2:35][S:36](=[O:37])[C@H:31]12)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 704647027-Benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide

Produkt 1

HCID 70464442t-Butyl 7-benzamido-3-methyl-3-cephem-4-carboxylate 1-oxideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A mixture of 103.2 g of dicyclohexylcarbodiimide, 43.5 g of t-butanol and 1.1 g of cuprous chloride was stored for 3 days at room temperature and the resulting compound was dissolved into 200 ml of dichloromethane. The solution was added dropwise to a stirred suspension of 35 g of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 500 ml of dichloromethane and after stirring at room temperature for 24 hours, the obtained N,N'-dicyclohexyl urea was separated by filtration and washed with dichloromethane. The combined filtrate and washing liquid were extracted with a 2 N hydrochloric acid solution, a saturated sodium bicarbonate solution and twice with water. The dichloromethane was evaporated under vacuo and toluene was added to the residue. The obtained crystals were filtered off and were washed with toluene. After crystallization from a mixture of dichloromethane and toluene, 19.6 g of t-butyl 7-benzamido-3-methyl-3-cephem-4-carboxylate-1-oxide were obtained having the following characteristics:

Aufarbeitung

  1. customthe obtained N,N'-dicyclohexyl urea was separated by filtration
  2. washwashed with dichloromethane
  3. washThe combined filtrate and washing liquid
  4. extractionwere extracted with a 2 N hydrochloric acid solution
  5. customThe dichloromethane was evaporated under vacuo and toluene
  6. additionwas added to the residue
  7. filtrationThe obtained crystals were filtered off
  8. washwere washed with toluene
  9. customAfter crystallization
  10. additionfrom a mixture of dichloromethane and toluene

Quellen und Nachweise

ORD-Eintrag
ord-be1a76a6af0145c18390ffeb9c12a332
Quelldatensatz
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04347358

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion