4-Nitrophenol → Z-Pyr-ONp

HRID 543248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543248
[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22](O)[CH:21]=1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@H:12]1[C:17]([O:19][C:22]1[CH:21]=[CH:20][C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 9804-NitrophenolHCID 6376481-(Phenylmethyl) (2S)-5-oxo-1,2-pyrrolidinedicarboxylate

Produkt 1

HCID 7408213Z-Pyr-ONp

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

10 g (40 mmol) of N-(benzyloxycarbonyl)-(L)-pyroglutamic acid and 5.84 g (40 mmol) of p-nitrophenol are dissolved in 100 ml of THF. A solution of 8.65 g (42 mmol) of N,N-dicyclohexylcarbodiimide in 40 ml of THF is run in at ordinary temperature, the mixture is stirred for 6 hours and filtered, the filtrate is evaporated, the residue is taken up with ethyl acetate, the mixture is filtered, the filtrate is evaporated and the residue is recrystallized from the same solvent. This gives 60% of a pure product of melting point=141°-2° C.; [α]D25 =-48.7° (C=1, THF).

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate is evaporated
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated
  5. customthe residue is recrystallized from the same solvent
  6. custom[α]D25 =-48.7° (C=1, THF)

Quellen und Nachweise

ORD-Eintrag
ord-32af35763de847c0919cbdad45f8c8f0
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661512

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