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Water → Ethyl 4-[[4-[1-(1-Acetoxyethyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetate

HRID 993041
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 993041
Cl.Cl.[O:3]=[C:4]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:7][CH2:6][N:5]1[CH2:16][C:17]([C:19]1[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1)=[O:18].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[C:48](=O)([O:56]C1C=CC([N+]([O-])=O)=CC=1)[O:49][CH:50]([O:52][C:53](=[O:55])[CH3:54])[CH3:51].O>CN(C)C=O>[C:53]([O:52][CH:50]([O:49][C:48]([N:13]1[CH2:12][CH2:11][CH:10]([N:8]2[CH2:7][CH2:6][N:5]([CH2:16][C:17]([C:19]3[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=3)=[O:18])[C:4](=[O:3])[CH2:9]2)[CH2:15][CH2:14]1)=[O:56])[CH3:51])(=[O:55])[CH3:54]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 88675Proton spongeHCID 117805601-acetoxyethyl p-nitrophenyl carbonateHCID 18408903HCID 18408903, Verbindung

Produkt 1

HCID 18408908Ethyl 4-[[4-[1-(1-Acetoxyethyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 107 mg of ethyl 4-[[2-oxo-4-(piperidin-4-yl)piperazin-1-yl]acetyl]phenoxyacetate dihydrochloride synthesized according to the method described in WO962503 in 2 ml of N,N-dimethylformamide were added 110 mg of proton sponge and 85.7 mg of 1-acetoxyethyl 4-nitrophenyl carbonate with stirring at 0° C., and the mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into 2 ml of water and extracted three times with 4 ml of ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The residue thus obtained was purified by chromatography on an LH-20 column (chloroform:methanol=1:1) to give 119 mg of the title compound (100%).

Aufarbeitung

  1. customsynthesized
  2. stirringthe mixture was stirred at room temperature for 18 hours
  3. extractionextracted three times with 4 ml of ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue thus obtained
  7. customwas purified by chromatography on an LH-20 column (chloroform:methanol=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c4b5436f4a4144fbb1d2cb1f99bef700
Quelldatensatz
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06472397B1

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