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4-Methylmorpholine → HCID 131717889, Verbindung

HRID 324160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 324160
C([C:8]1[CH:23]=[C:22]([NH:24][NH:25][C:26]([NH2:28])=[S:27])[CH:21]=[CH:20][C:9]=1[C:10]([O:12][N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19])=[O:11])(OC(C)(C)C)=O.CN1CCOCC1.C(=O)(OC(Cl)C(Cl)(Cl)[Cl:48])ON1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C.CCOCC>[ClH:48].[NH:24]([C:22]1[CH:23]=[CH:8][C:9]([C:10]([O:12][N:13]2[C:17](=[O:18])[CH2:16][CH2:15][C:14]2=[O:19])=[O:11])=[CH:20][CH:21]=1)[NH:25][C:26]([NH2:28])=[S:27].[C:14]1(=[O:19])[N:13]([O:12][C:10](=[O:11])[C:9]2[CH:20]=[CH:21][C:22]([NH:24][NH:25][C:26]([NH2:28])=[S:27])=[CH:23][CH:8]=2)[C:17](=[O:18])[CH2:16][CH2:15]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 13670087N-(1,2,2,2-Tetrachloroethoxycarbonyloxy)succinimideHCID 88219684HCID 88219684, Verbindung

Produkt 1

HCID 131717889HCID 131717889, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Synthesis of Succinimidyl BOC-4-thiosemicarbazidobenzoate [Hydrazinecarboxylic acid, 2-[[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxyl]carbonyl]phenyl]amino]thioxomethyl]-1,1-dimethylethyl ester]—To a solution of acid (1 equivalent) and N-methylmorpholine (1.1 equivalents) in acetonitrile was added a solution of succinimidyl tetrachloroethyl carbonate (1 equivalent) in acetonitrile. The reaction mixture was stirred at room temperature for 16 hours. Ethyl acetate was added to the reaction mixture and the homogeneous solution was washed with cold 5% citric acid, cold water, cold aqueous saturated sodium bicarbonate solution, cold water and cold brine. The organic phase was dried (MgSO4), filtered and concentrated to give a pale yellow oil. The oil was flash chromatographed on silica gel using hexanes/ethyl acetate as eluant. The product was isolated as a yellow oil which solidified on the addition of ether. The solids were isolated by filtration to give the desired product; yield 25%; m.p. 161-163°.

Aufarbeitung

  1. washthe homogeneous solution was washed with cold 5% citric acid, cold water, cold aqueous saturated sodium bicarbonate solution, cold water and cold brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a pale yellow oil
  6. customchromatographed on silica gel
  7. customThe product was isolated as a yellow oil which
  8. customThe solids were isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-ddcfbea3febe461cb1a2ef3be433772d
Quelldatensatz
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06217845B1

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