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4-Nitrophenol → N-((Phenylmethoxy)carbonyl)glycine 4-nitrophenyl ester

HRID 1439412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1439412
C1(OP(O)OC2C=CC=CC=2)C=CC=CC=1.[CH:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[C:19]([OH:26])[CH:18]=1.[NH:27]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH2:28][C:29](O)=[O:30]>N1C=CC=CC=1>[N+:23]([C:22]1[CH:21]=[CH:20][C:19]([O:26][C:29](=[O:30])[CH2:28][NH:27][C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[O:33])=[CH:18][CH:17]=1)([O-:25])=[O:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 9804-NitrophenolHCID 14349BenzyloxycarbonylglycineHCID 426896Phosphorous diphenyl ester

Produkt 1

HCID 15616N-((Phenylmethoxy)carbonyl)glycine 4-nitrophenyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel4×

Versuchsvorschrift

A mixture of 2.93 g. (0.0125 mole) of phosphorous diphenyl ester and 3.37 g. (0.0125 mole) of mercuric chloride was refluxed for 1 hour in 20 ml. of pyridine. Thereafter, 1.74 g. (0.0125 mole) of p-nitrophenol and 10 ml. of pyridine were added, and the mixture was further reacted for 1 hour. To the reaction mixture were added 2.61 g. (0.0125 mole) of Z-Gly.OH having an amino group protected with Z and 10 ml. of pyridine, and the mixture was reacted under reflux for 1 hour. After completion of the reaction, pyridine was removed by distillation under reduced pressure, and the residue was extracted with 100 ml. of ethyl acetate. The ethyl acetate layer was washed with 2N-HCl, a saturated aqueous NaHCO3 solution and water in this order and then dried over anhydrous Na2SO4, and thereafter ethyl acetate was removed by distillation under reduced pressure. The resulting residue was allowed to stand to form a solid, which was then recrystallized from ethanol to obtain N-benzyloxycarbonyl glycine p-nitrophenyl ester (hereinafter represented by ##STR9## in a yield of 75% (3.0 g.).

Aufarbeitung

  1. additionA mixture of 2.93 g
  2. customthe mixture was further reacted for 1 hour
  3. additionTo the reaction mixture were added 2.61 g
  4. temperatureunder reflux for 1 hour
  5. customwas removed by distillation under reduced pressure
  6. extractionthe residue was extracted with 100 ml
  7. washThe ethyl acetate layer was washed with 2N-HCl
  8. dry with materiala saturated aqueous NaHCO3 solution and water in this order and then dried over anhydrous Na2SO4
  9. customethyl acetate was removed by distillation under reduced pressure
  10. customto form a solid, which
  11. customwas then recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fcb33f8a7272428888da4fd338b05ff6
Quelldatensatz
uspto-grants-1977_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04059603

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