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Glycolic Acid → HCID 13344954, Verbindung

HRID 1462237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1462237
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:28]OC(=O)C(C)(C)C)[C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:17][CH:16]=2)[C:10](=[O:36])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]([OH:42])(=[O:41])[CH2:39][OH:40].Cl.C(O)C>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:28][O:40][CH2:39][C:38]([OH:42])=[O:41])[C:22]3[N:23]=[CH:24][CH:25]=[CH:26][N:27]=3)=[CH:17][CH:16]=2)[C:10](=[O:36])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 757Glycolic AcidHCID 13210503HCID 13210503, VerbindungHCID 21887872Ethanol hydrochloride

Produkt 1

HCID 13344954HCID 13344954, VerbindungAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 30 ml of ethyl acetate was dissolved 1 g of 1-benzyl-4-{4-[N-pivaloyloxymethyl-N-(2-pyrimidinyl)-amino]benzyl}-2,3-dioxopiperazine, and 1 g of glycolic acid and 0.02 ml of N hydrogen chloride-ethanol solution were added, after which the resulting mixture was subjected to reaction at room temperature for 3 hours with stirring. After the completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was extracted with 100 ml of methylene chloride. The methylene chloride layer was washed with 30 ml of water and then 30 ml of saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (Wakogel C-200, eluted with chloroformethanol), and recrystallized from ethyl acetate-diisopropyl ether, to obtain 0.5 g (52.8% yield) of 1-benzyl-4-{4-[N-carboxymethoxymethyl-N-(2-pyrimidinyl)amino]benzyl}-2,3-dioxopiperazine having a melting point of 85° to 90° C.

Aufarbeitung

  1. additionwere added
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 3 hours
  3. customAfter the completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. extractionwas extracted with 100 ml of methylene chloride
  7. washThe methylene chloride layer was washed with 30 ml of water
  8. dry with material30 ml of saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  9. customafter which the solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by a column chromatography (Wakogel C-200, eluted with chloroformethanol)
  12. customrecrystallized from ethyl acetate-diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-40508d78a0c34cefa67c057da49c6def
Quelldatensatz
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04459407

Notizen zur Reaktion

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